diff --git a/crates/compiler/fmt/src/annotation.rs b/crates/compiler/fmt/src/annotation.rs
index 4bbe98a4d5..73ed08a605 100644
--- a/crates/compiler/fmt/src/annotation.rs
+++ b/crates/compiler/fmt/src/annotation.rs
@@ -12,7 +12,7 @@ use roc_region::all::Loc;
 
 /// Does an AST node need parens around it?
 ///
-/// Usually not, but there are two cases where it may be required
+/// Usually not, but there are a few cases where it may be required
 ///
 /// 1. In a function type, function types are in parens
 ///
@@ -25,11 +25,19 @@ use roc_region::all::Loc;
 ///     Just (Just a)
 ///     List (List a)
 ///     reverse (reverse l)
+///
+///  3. In a chain of binary operators, things like nested defs require parens.
+///
+///    a + (
+///       x = 3
+///       x + 1
+///    )
 #[derive(PartialEq, Eq, Clone, Copy, Debug)]
 pub enum Parens {
     NotNeeded,
     InFunctionType,
     InApply,
+    InOperator,
 }
 
 /// In an AST node, do we show newlines around it
@@ -263,7 +271,6 @@ impl<'a> Formattable for TypeAnnotation<'a> {
             }
             Apply(pkg, name, arguments) => {
                 buf.indent(indent);
-                // NOTE apply is never multiline
                 let write_parens = parens == Parens::InApply && !arguments.is_empty();
 
                 if write_parens {
@@ -277,11 +284,38 @@ impl<'a> Formattable for TypeAnnotation<'a> {
 
                 buf.push_str(name);
 
-                for argument in *arguments {
-                    buf.spaces(1);
-                    argument
-                        .value
-                        .format_with_options(buf, Parens::InApply, Newlines::No, indent);
+                let needs_indent = except_last(arguments).any(|a| a.is_multiline())
+                    || arguments
+                        .last()
+                        .map(|a| {
+                            a.is_multiline()
+                                && (!a.extract_spaces().before.is_empty()
+                                    || !is_outdentable(&a.value))
+                        })
+                        .unwrap_or_default();
+
+                let arg_indent = if needs_indent {
+                    indent + INDENT
+                } else {
+                    indent
+                };
+
+                for arg in arguments.iter() {
+                    if needs_indent {
+                        let arg = arg.extract_spaces();
+                        fmt_spaces(buf, arg.before.iter(), arg_indent);
+                        buf.ensure_ends_with_newline();
+                        arg.item.format_with_options(
+                            buf,
+                            Parens::InApply,
+                            Newlines::Yes,
+                            arg_indent,
+                        );
+                        fmt_spaces(buf, arg.after.iter(), arg_indent);
+                    } else {
+                        buf.spaces(1);
+                        arg.format_with_options(buf, Parens::InApply, Newlines::No, arg_indent);
+                    }
                 }
 
                 if write_parens {
@@ -372,6 +406,13 @@ impl<'a> Formattable for TypeAnnotation<'a> {
     }
 }
 
+fn is_outdentable(ann: &TypeAnnotation) -> bool {
+    matches!(
+        ann.extract_spaces().item,
+        TypeAnnotation::Tuple { .. } | TypeAnnotation::Record { .. }
+    )
+}
+
 /// Fields are subtly different on the type and term level:
 ///
 /// >   type: { x : Int, y : Bool }
@@ -691,3 +732,11 @@ impl<'a> Formattable for HasAbilities<'a> {
         }
     }
 }
+
+pub fn except_last<T>(items: &[T]) -> impl Iterator<Item = &T> {
+    if items.is_empty() {
+        items.iter()
+    } else {
+        items[..items.len() - 1].iter()
+    }
+}
diff --git a/crates/compiler/fmt/src/def.rs b/crates/compiler/fmt/src/def.rs
index 49de57caac..b2757aee3c 100644
--- a/crates/compiler/fmt/src/def.rs
+++ b/crates/compiler/fmt/src/def.rs
@@ -77,6 +77,7 @@ impl<'a> Formattable for TypeDef<'a> {
                 for var in *vars {
                     buf.spaces(1);
                     fmt_pattern(buf, &var.value, indent, Parens::NotNeeded);
+                    buf.indent(indent);
                 }
 
                 buf.push_str(" :");
@@ -95,6 +96,7 @@ impl<'a> Formattable for TypeDef<'a> {
                 for var in *vars {
                     buf.spaces(1);
                     fmt_pattern(buf, &var.value, indent, Parens::NotNeeded);
+                    buf.indent(indent);
                 }
 
                 buf.push_str(" :=");
@@ -136,6 +138,7 @@ impl<'a> Formattable for TypeDef<'a> {
                 for var in *vars {
                     buf.spaces(1);
                     fmt_pattern(buf, &var.value, indent, Parens::NotNeeded);
+                    buf.indent(indent);
                 }
 
                 buf.push_str(" has");
@@ -191,6 +194,7 @@ impl<'a> Formattable for ValueDef<'a> {
         match self {
             Annotation(loc_pattern, loc_annotation) => {
                 loc_pattern.format(buf, indent);
+                buf.indent(indent);
 
                 if loc_annotation.is_multiline() {
                     buf.push_str(" :");
@@ -390,6 +394,7 @@ pub fn fmt_body<'a, 'buf>(
     indent: u16,
 ) {
     pattern.format_with_options(buf, Parens::InApply, Newlines::No, indent);
+    buf.indent(indent);
     buf.push_str(" =");
 
     if body.is_multiline() {
@@ -415,7 +420,7 @@ pub fn fmt_body<'a, 'buf>(
                     );
                 }
             }
-            Expr::BinOps(_, _) => {
+            Expr::Defs(..) | Expr::BinOps(_, _) => {
                 // Binop chains always get a newline. Otherwise you can have things like:
                 //
                 //     something = foo
diff --git a/crates/compiler/fmt/src/expr.rs b/crates/compiler/fmt/src/expr.rs
index 7b0330b55c..1fc7a90032 100644
--- a/crates/compiler/fmt/src/expr.rs
+++ b/crates/compiler/fmt/src/expr.rs
@@ -1,4 +1,4 @@
-use crate::annotation::{Formattable, Newlines, Parens};
+use crate::annotation::{except_last, Formattable, Newlines, Parens};
 use crate::collection::{fmt_collection, Braces};
 use crate::def::fmt_defs;
 use crate::pattern::fmt_pattern;
@@ -142,7 +142,7 @@ impl<'a> Formattable for Expr<'a> {
             }
             ParensAround(sub_expr) => {
                 if parens == Parens::NotNeeded && !sub_expr_requests_parens(sub_expr) {
-                    sub_expr.format_with_options(buf, Parens::NotNeeded, Newlines::Yes, indent);
+                    sub_expr.format_with_options(buf, Parens::NotNeeded, newlines, indent);
                 } else {
                     let should_add_newlines = match sub_expr {
                         Expr::Closure(..)
@@ -202,86 +202,111 @@ impl<'a> Formattable for Expr<'a> {
                 buf.push_str("crash");
             }
             Apply(loc_expr, loc_args, _) => {
+                // Sadly this assertion fails in practice. The fact that the parser produces code like this is going to
+                // confuse the formatter, because it depends on being able to "see" spaces that logically come before the inner
+                // expr in several places - which is necessarily the case when the `loc_expr` of the apply itself has
+                // SpaceBefore.
+                //
+                // TODO: enforce in the type system that spaces must be pushed to the "outside".
+                // In other words, Expr::Apply should look something like the following, and there shouldn't be Expr::SpaceBefore and ::SpaceAfter.
+                //
+                // ```
+                // Apply(&'a SpaceAfter<Loc<Expr<'a>>>, &'a [&'a SpaceBefore<Loc<Expr<'a>>>], CalledVia),
+                // ```
+                //
+                // assert!(loc_expr.extract_spaces().before.is_empty(), "{:#?}", self);
+
                 buf.indent(indent);
                 if apply_needs_parens && !loc_args.is_empty() {
                     buf.push('(');
                 }
 
+                // should_reflow_outdentable, aka should we transform this:
+                //
+                // ```
+                // foo bar
+                //   [
+                //     1,
+                //     2,
+                //   ]
+                // ```
+                //
+                // Into this:
+                //
+                // ```
+                // foo bar [
+                //   1,
+                //   2,
+                // ]
+                // ```
+                let should_reflow_outdentable = loc_expr.extract_spaces().after.is_empty()
+                    && except_last(loc_args).all(|a| !a.is_multiline())
+                    && loc_args
+                        .last()
+                        .map(|a| {
+                            a.extract_spaces().item.is_multiline()
+                                && matches!(
+                                    a.value.extract_spaces().item,
+                                    Expr::Tuple(_) | Expr::List(_) | Expr::Record(_)
+                                )
+                                && a.extract_spaces().before == [CommentOrNewline::Newline]
+                        })
+                        .unwrap_or_default();
+
+                let needs_indent = !should_reflow_outdentable
+                    && (!loc_expr.extract_spaces().after.is_empty()
+                        || except_last(loc_args).any(|a| a.is_multiline())
+                        || loc_args
+                            .last()
+                            .map(|a| {
+                                a.is_multiline()
+                                    && (!a.extract_spaces().before.is_empty()
+                                        || !is_outdentable(&a.value))
+                            })
+                            .unwrap_or_default());
+
+                let arg_indent = if needs_indent {
+                    indent + INDENT
+                } else {
+                    indent
+                };
+
                 loc_expr.format_with_options(buf, Parens::InApply, Newlines::Yes, indent);
 
-                let multiline_args = loc_args.iter().any(|loc_arg| loc_arg.is_multiline());
+                for loc_arg in loc_args.iter() {
+                    if should_reflow_outdentable {
+                        buf.spaces(1);
 
-                let mut found_multiline_expr = false;
-                let mut iter = loc_args.iter().peekable();
+                        // Ignore any comments+newlines before/after.
+                        // We checked above that there's only a single newline before the last arg,
+                        // which we're intentionally ignoring.
 
-                while let Some(loc_arg) = iter.next() {
-                    if iter.peek().is_none() {
-                        found_multiline_expr = match loc_arg.value {
-                            SpaceBefore(sub_expr, spaces) => match sub_expr {
-                                Record { .. } | List { .. } => {
-                                    let is_only_newlines = spaces.iter().all(|s| s.is_newline());
-                                    is_only_newlines
-                                        && !found_multiline_expr
-                                        && sub_expr.is_multiline()
-                                }
-                                _ => false,
-                            },
-                            Record { .. } | List { .. } | Closure { .. } => {
-                                !found_multiline_expr && loc_arg.is_multiline()
-                            }
-                            _ => false,
-                        }
+                        let arg = loc_arg.extract_spaces();
+                        arg.item.format_with_options(
+                            buf,
+                            Parens::InApply,
+                            Newlines::Yes,
+                            arg_indent,
+                        );
+                    } else if needs_indent {
+                        let arg = loc_arg.extract_spaces();
+                        fmt_spaces(buf, arg.before.iter(), arg_indent);
+                        buf.ensure_ends_with_newline();
+                        arg.item.format_with_options(
+                            buf,
+                            Parens::InApply,
+                            Newlines::Yes,
+                            arg_indent,
+                        );
+                        fmt_spaces(buf, arg.after.iter(), arg_indent);
                     } else {
-                        found_multiline_expr = loc_arg.is_multiline();
-                    }
-                }
-
-                let should_outdent_last_arg = found_multiline_expr;
-
-                if multiline_args && !should_outdent_last_arg {
-                    let arg_indent = indent + INDENT;
-
-                    for loc_arg in loc_args.iter() {
-                        buf.newline();
-                        loc_arg.format_with_options(buf, Parens::InApply, Newlines::No, arg_indent);
-                    }
-                } else if multiline_args && should_outdent_last_arg {
-                    let mut iter = loc_args.iter().peekable();
-                    while let Some(loc_arg) = iter.next() {
                         buf.spaces(1);
-
-                        if iter.peek().is_none() {
-                            match loc_arg.value {
-                                SpaceBefore(sub_expr, _) => {
-                                    sub_expr.format_with_options(
-                                        buf,
-                                        Parens::InApply,
-                                        Newlines::Yes,
-                                        indent,
-                                    );
-                                }
-                                _ => {
-                                    loc_arg.format_with_options(
-                                        buf,
-                                        Parens::InApply,
-                                        Newlines::Yes,
-                                        indent,
-                                    );
-                                }
-                            }
-                        } else {
-                            loc_arg.format_with_options(
-                                buf,
-                                Parens::InApply,
-                                Newlines::Yes,
-                                indent,
-                            );
-                        }
-                    }
-                } else {
-                    for loc_arg in loc_args.iter() {
-                        buf.spaces(1);
-                        loc_arg.format_with_options(buf, Parens::InApply, Newlines::Yes, indent);
+                        loc_arg.format_with_options(
+                            buf,
+                            Parens::InApply,
+                            Newlines::Yes,
+                            arg_indent,
+                        );
                     }
                 }
 
@@ -337,24 +362,28 @@ impl<'a> Formattable for Expr<'a> {
                 fmt_backpassing(buf, loc_patterns, loc_body, loc_ret, indent);
             }
             Defs(defs, ret) => {
-                // It should theoretically be impossible to *parse* an empty defs list.
-                // (Canonicalization can remove defs later, but that hasn't happened yet!)
-                debug_assert!(!defs.is_empty());
+                {
+                    let indent = if parens == Parens::InOperator {
+                        buf.indent(indent);
+                        buf.push('(');
+                        buf.newline();
+                        indent + INDENT
+                    } else {
+                        indent
+                    };
 
-                fmt_defs(buf, defs, indent);
+                    // It should theoretically be impossible to *parse* an empty defs list.
+                    // (Canonicalization can remove defs later, but that hasn't happened yet!)
+                    debug_assert!(!defs.is_empty());
 
-                match &ret.value {
-                    SpaceBefore(sub_expr, spaces) => {
-                        let empty_line_before_return = empty_line_before_expr(&ret.value);
-                        let has_inline_comment = has_line_comment_before(&ret.value);
+                    fmt_defs(buf, defs, indent);
 
-                        if has_inline_comment {
+                    match &ret.value {
+                        SpaceBefore(sub_expr, spaces) => {
                             buf.spaces(1);
-                            format_spaces(buf, spaces, newlines, indent);
+                            fmt_spaces(buf, spaces.iter(), indent);
 
-                            if !empty_line_before_return {
-                                buf.newline();
-                            }
+                            buf.indent(indent);
 
                             sub_expr.format_with_options(
                                 buf,
@@ -362,17 +391,21 @@ impl<'a> Formattable for Expr<'a> {
                                 Newlines::Yes,
                                 indent,
                             );
-                        } else {
+                        }
+                        _ => {
+                            buf.ensure_ends_with_newline();
+                            buf.indent(indent);
+                            // Even if there were no defs, which theoretically should never happen,
+                            // still print the return value.
                             ret.format_with_options(buf, Parens::NotNeeded, Newlines::Yes, indent);
                         }
                     }
-                    _ => {
-                        buf.ensure_ends_with_newline();
-                        buf.indent(indent);
-                        // Even if there were no defs, which theoretically should never happen,
-                        // still print the return value.
-                        ret.format_with_options(buf, Parens::NotNeeded, Newlines::Yes, indent);
-                    }
+                }
+
+                if parens == Parens::InOperator {
+                    buf.ensure_ends_with_newline();
+                    buf.indent(indent);
+                    buf.push(')');
                 }
             }
             Expect(condition, continuation) => {
@@ -387,7 +420,7 @@ impl<'a> Formattable for Expr<'a> {
             When(loc_condition, branches) => fmt_when(buf, loc_condition, branches, indent),
             Tuple(items) => fmt_collection(buf, indent, Braces::Round, *items, Newlines::No),
             List(items) => fmt_collection(buf, indent, Braces::Square, *items, Newlines::No),
-            BinOps(lefts, right) => fmt_binops(buf, lefts, right, false, parens, indent),
+            BinOps(lefts, right) => fmt_binops(buf, lefts, right, false, indent),
             UnaryOp(sub_expr, unary_op) => {
                 buf.indent(indent);
                 match &unary_op.value {
@@ -461,6 +494,13 @@ pub(crate) fn format_sq_literal(buf: &mut Buf, s: &str) {
     buf.push('\'');
 }
 
+fn is_outdentable(expr: &Expr) -> bool {
+    matches!(
+        expr.extract_spaces().item,
+        Expr::Tuple(_) | Expr::List(_) | Expr::Record(_) | Expr::Closure(..)
+    )
+}
+
 fn starts_with_newline(expr: &Expr) -> bool {
     use roc_parse::ast::Expr::*;
 
@@ -599,7 +639,6 @@ fn fmt_binops<'a, 'buf>(
     lefts: &'a [(Loc<Expr<'a>>, Loc<BinOp>)],
     loc_right_side: &'a Loc<Expr<'a>>,
     part_of_multi_line_binops: bool,
-    apply_needs_parens: Parens,
     indent: u16,
 ) {
     let is_multiline = part_of_multi_line_binops
@@ -609,7 +648,7 @@ fn fmt_binops<'a, 'buf>(
     for (loc_left_side, loc_binop) in lefts {
         let binop = loc_binop.value;
 
-        loc_left_side.format_with_options(buf, apply_needs_parens, Newlines::No, indent);
+        loc_left_side.format_with_options(buf, Parens::InOperator, Newlines::No, indent);
 
         if is_multiline {
             buf.ensure_ends_with_newline();
@@ -623,7 +662,7 @@ fn fmt_binops<'a, 'buf>(
         buf.spaces(1);
     }
 
-    loc_right_side.format_with_options(buf, apply_needs_parens, Newlines::Yes, indent);
+    loc_right_side.format_with_options(buf, Parens::InOperator, Newlines::Yes, indent);
 }
 
 fn format_spaces<'a, 'buf>(
@@ -642,44 +681,6 @@ fn format_spaces<'a, 'buf>(
     }
 }
 
-fn has_line_comment_before<'a>(expr: &'a Expr<'a>) -> bool {
-    use roc_parse::ast::Expr::*;
-
-    match expr {
-        SpaceBefore(_, spaces) => {
-            matches!(spaces.iter().next(), Some(CommentOrNewline::LineComment(_)))
-        }
-        _ => false,
-    }
-}
-
-fn empty_line_before_expr<'a>(expr: &'a Expr<'a>) -> bool {
-    use roc_parse::ast::Expr::*;
-
-    match expr {
-        SpaceBefore(_, spaces) => {
-            let mut has_at_least_one_newline = false;
-
-            for comment_or_newline in spaces.iter() {
-                match comment_or_newline {
-                    CommentOrNewline::Newline => {
-                        if has_at_least_one_newline {
-                            return true;
-                        } else {
-                            has_at_least_one_newline = true;
-                        }
-                    }
-                    CommentOrNewline::LineComment(_) | CommentOrNewline::DocComment(_) => {}
-                }
-            }
-
-            false
-        }
-
-        _ => false,
-    }
-}
-
 fn is_when_patterns_multiline(when_branch: &WhenBranch) -> bool {
     let patterns = when_branch.patterns;
     let (first_pattern, rest) = patterns.split_first().unwrap();
@@ -1204,19 +1205,16 @@ fn fmt_backpassing<'a, 'buf>(
         indent
     };
 
-    let pattern_needs_parens = loc_patterns
-        .iter()
-        .any(|p| pattern_needs_parens_when_backpassing(&p.value));
-
-    if pattern_needs_parens {
-        buf.indent(indent);
-        buf.push('(');
-    }
-
     let mut it = loc_patterns.iter().peekable();
 
     while let Some(loc_pattern) = it.next() {
-        loc_pattern.format(buf, indent);
+        let needs_parens = if pattern_needs_parens_when_backpassing(&loc_pattern.value) {
+            Parens::InApply
+        } else {
+            Parens::NotNeeded
+        };
+
+        loc_pattern.format_with_options(buf, needs_parens, Newlines::No, indent);
 
         if it.peek().is_some() {
             if arguments_are_multiline {
@@ -1229,10 +1227,6 @@ fn fmt_backpassing<'a, 'buf>(
         }
     }
 
-    if pattern_needs_parens {
-        buf.push(')');
-    }
-
     if arguments_are_multiline {
         buf.newline();
         buf.indent(indent);
@@ -1479,6 +1473,8 @@ fn sub_expr_requests_parens(expr: &Expr<'_>) -> bool {
                 })
         }
         Expr::If(_, _) => true,
+        Expr::SpaceBefore(e, _) => sub_expr_requests_parens(e),
+        Expr::SpaceAfter(e, _) => sub_expr_requests_parens(e),
         _ => false,
     }
 }
diff --git a/crates/compiler/fmt/src/spaces.rs b/crates/compiler/fmt/src/spaces.rs
index b9c9ad5e99..b91fcad716 100644
--- a/crates/compiler/fmt/src/spaces.rs
+++ b/crates/compiler/fmt/src/spaces.rs
@@ -72,12 +72,11 @@ fn fmt_spaces_max_consecutive_newlines<'a, 'buf, I>(
     // Only ever print two newlines back to back.
     // (Two newlines renders as one blank line.)
     let mut consecutive_newlines = 0;
-    let mut encountered_comment = false;
 
     for space in spaces {
         match space {
             Newline => {
-                if !encountered_comment && (consecutive_newlines < max_consecutive_newlines) {
+                if consecutive_newlines < max_consecutive_newlines {
                     buf.newline();
 
                     // Don't bother incrementing it if we're already over the limit.
@@ -90,14 +89,14 @@ fn fmt_spaces_max_consecutive_newlines<'a, 'buf, I>(
                 fmt_comment(buf, comment);
                 buf.newline();
 
-                encountered_comment = true;
+                consecutive_newlines = 1;
             }
             DocComment(docs) => {
                 buf.indent(indent);
                 fmt_docs(buf, docs);
                 buf.newline();
 
-                encountered_comment = true;
+                consecutive_newlines = 1;
             }
         }
     }
diff --git a/crates/compiler/parse/src/ast.rs b/crates/compiler/parse/src/ast.rs
index 9a59d2134e..35907841ea 100644
--- a/crates/compiler/parse/src/ast.rs
+++ b/crates/compiler/parse/src/ast.rs
@@ -1,7 +1,6 @@
 use std::fmt::Debug;
 
 use crate::header::{AppHeader, HostedHeader, InterfaceHeader, PackageHeader, PlatformHeader};
-use crate::ident::Ident;
 use crate::parser::ESingleQuote;
 use bumpalo::collections::{String, Vec};
 use bumpalo::Bump;
@@ -807,51 +806,6 @@ pub enum Base {
 }
 
 impl<'a> Pattern<'a> {
-    pub fn from_ident(arena: &'a Bump, ident: Ident<'a>) -> Pattern<'a> {
-        match ident {
-            Ident::Tag(string) => Pattern::Tag(string),
-            Ident::OpaqueRef(string) => Pattern::OpaqueRef(string),
-            Ident::Access { module_name, parts } => {
-                if parts.len() == 1 {
-                    // This is valid iff there is no module.
-                    let ident = parts.iter().next().unwrap();
-
-                    if module_name.is_empty() {
-                        Pattern::Identifier(ident)
-                    } else {
-                        Pattern::QualifiedIdentifier { module_name, ident }
-                    }
-                } else {
-                    // This is definitely malformed.
-                    let mut buf =
-                        String::with_capacity_in(module_name.len() + (2 * parts.len()), arena);
-                    let mut any_parts_printed = if module_name.is_empty() {
-                        false
-                    } else {
-                        buf.push_str(module_name);
-
-                        true
-                    };
-
-                    for part in parts.iter() {
-                        if any_parts_printed {
-                            buf.push('.');
-                        } else {
-                            any_parts_printed = true;
-                        }
-
-                        buf.push_str(part);
-                    }
-
-                    Pattern::Malformed(buf.into_bump_str())
-                }
-            }
-            Ident::RecordAccessorFunction(string) => Pattern::Malformed(string),
-            Ident::TupleAccessorFunction(string) => Pattern::Malformed(string),
-            Ident::Malformed(string, _problem) => Pattern::Malformed(string),
-        }
-    }
-
     /// Check that patterns are equivalent, meaning they have the same shape, but may have
     /// different locations/whitespace
     pub fn equivalent(&self, other: &Self) -> bool {
diff --git a/crates/compiler/parse/src/blankspace.rs b/crates/compiler/parse/src/blankspace.rs
index 8a72dbbd79..64ee7f1b8a 100644
--- a/crates/compiler/parse/src/blankspace.rs
+++ b/crates/compiler/parse/src/blankspace.rs
@@ -378,6 +378,10 @@ where
     }
 }
 
+fn begins_with_crlf(bytes: &[u8]) -> bool {
+    bytes.len() >= 2 && bytes[0] == b'\r' && bytes[1] == b'\n'
+}
+
 pub fn spaces<'a, E>() -> impl Parser<'a, &'a [CommentOrNewline<'a>], E>
 where
     E: 'a + SpaceProblem,
@@ -399,6 +403,7 @@ where
                     let is_doc_comment = state.bytes().first() == Some(&b'#')
                         && (state.bytes().get(1) == Some(&b' ')
                             || state.bytes().get(1) == Some(&b'\n')
+                            || begins_with_crlf(&state.bytes()[1..])
                             || state.bytes().get(1) == None);
 
                     if is_doc_comment {
@@ -422,7 +427,10 @@ where
                     newlines.push(comment);
                     state.advance_mut(len);
 
-                    if state.bytes().first() == Some(&b'\n') {
+                    if begins_with_crlf(state.bytes()) {
+                        state.advance_mut(1);
+                        state = state.advance_newline();
+                    } else if state.bytes().first() == Some(&b'\n') {
                         state = state.advance_newline();
                     }
 
diff --git a/crates/compiler/parse/src/expr.rs b/crates/compiler/parse/src/expr.rs
index c5f86de8f2..662ae6ef4f 100644
--- a/crates/compiler/parse/src/expr.rs
+++ b/crates/compiler/parse/src/expr.rs
@@ -4,7 +4,7 @@ use crate::ast::{
 };
 use crate::blankspace::{
     space0_after_e, space0_around_e_no_after_indent_check, space0_around_ee, space0_before_e,
-    space0_e, spaces, spaces_around, spaces_before,
+    space0_before_optional_after, space0_e, spaces, spaces_around, spaces_before,
 };
 use crate::ident::{integer_ident, lowercase_ident, parse_ident, Accessor, Ident};
 use crate::keyword;
@@ -42,7 +42,7 @@ pub fn test_parse_expr<'a>(
     state: State<'a>,
 ) -> Result<Loc<Expr<'a>>, EExpr<'a>> {
     let parser = skip_second!(
-        space0_before_e(loc_expr(true), EExpr::IndentStart,),
+        space0_before_optional_after(loc_expr(true), EExpr::IndentStart, EExpr::IndentEnd),
         expr_end()
     );
 
@@ -255,7 +255,10 @@ fn loc_possibly_negative_or_negated_term<'a>(
         // this will parse negative numbers, which the unary negate thing up top doesn't (for now)
         loc!(specialize(EExpr::Number, number_literal_help())),
         loc!(map_with_arena!(
-            and!(loc!(word1(b'!', EExpr::Start)), loc_term(options)),
+            and!(
+                loc!(word1(b'!', EExpr::Start)),
+                space0_before_e(loc_term(options), EExpr::IndentStart)
+            ),
             |arena: &'a Bump, (loc_op, loc_expr): (Loc<_>, _)| {
                 Expr::UnaryOp(arena.alloc(loc_expr), Loc::at(loc_op.region, UnaryOp::Not))
             }
@@ -668,7 +671,7 @@ pub fn parse_single_def<'a>(
                     let (_, ann_type, state) = parser.parse(arena, state, min_indent)?;
                     let region = Region::span_across(&loc_pattern.region, &ann_type.region);
 
-                    match &loc_pattern.value {
+                    match &loc_pattern.value.extract_spaces().item {
                         Pattern::Apply(
                             Loc {
                                 value: Pattern::Tag(name),
@@ -740,7 +743,7 @@ pub fn parse_single_def<'a>(
                         opaque_signature_with_space_before().parse(arena, state, min_indent + 1)?;
                     let region = Region::span_across(&loc_pattern.region, &signature.region);
 
-                    match &loc_pattern.value {
+                    match &loc_pattern.value.extract_spaces().item {
                         Pattern::Apply(
                             Loc {
                                 value: Pattern::Tag(name),
@@ -1890,7 +1893,7 @@ fn expr_to_pattern_help<'a>(arena: &'a Bump, expr: &Expr<'a>) -> Result<Pattern<
 
         Expr::Str(string) => Ok(Pattern::StrLiteral(*string)),
         Expr::SingleQuote(string) => Ok(Pattern::SingleQuote(string)),
-        Expr::MalformedIdent(string, _problem) => Ok(Pattern::Malformed(string)),
+        Expr::MalformedIdent(string, problem) => Ok(Pattern::MalformedIdent(string, *problem)),
     }
 }
 
diff --git a/crates/compiler/parse/src/ident.rs b/crates/compiler/parse/src/ident.rs
index 0a4b772218..283d5c2d52 100644
--- a/crates/compiler/parse/src/ident.rs
+++ b/crates/compiler/parse/src/ident.rs
@@ -290,6 +290,10 @@ fn chomp_integer_part(buffer: &[u8]) -> Result<&str, Progress> {
     )
 }
 
+fn is_plausible_ident_continue(ch: char) -> bool {
+    ch == '_' || is_alnum(ch)
+}
+
 #[inline(always)]
 fn chomp_part<F, G>(leading_is_good: F, rest_is_good: G, buffer: &[u8]) -> Result<&str, Progress>
 where
@@ -317,6 +321,15 @@ where
         }
     }
 
+    if let Ok((next, _width)) = char::from_utf8_slice_start(&buffer[chomped..]) {
+        // This would mean we have e.g.:
+        // * identifier followed by a _
+        // * an integer followed by an alphabetic char
+        if is_plausible_ident_continue(next) {
+            return Err(NoProgress);
+        }
+    }
+
     if chomped == 0 {
         Err(NoProgress)
     } else {
diff --git a/crates/compiler/parse/src/parser.rs b/crates/compiler/parse/src/parser.rs
index 46dd7f2539..9dc715d74f 100644
--- a/crates/compiler/parse/src/parser.rs
+++ b/crates/compiler/parse/src/parser.rs
@@ -535,6 +535,9 @@ pub enum EPattern<'a> {
     IndentStart(Position),
     IndentEnd(Position),
     AsIndentStart(Position),
+
+    RecordAccessorFunction(Position),
+    TupleAccessorFunction(Position),
 }
 
 #[derive(Debug, Clone, PartialEq, Eq)]
diff --git a/crates/compiler/parse/src/pattern.rs b/crates/compiler/parse/src/pattern.rs
index 79896766db..197194dfcf 100644
--- a/crates/compiler/parse/src/pattern.rs
+++ b/crates/compiler/parse/src/pattern.rs
@@ -406,13 +406,13 @@ fn loc_ident_pattern_help<'a>(
                     ))
                 }
             }
-            Ident::RecordAccessorFunction(string) | Ident::TupleAccessorFunction(string) => Ok((
+            Ident::RecordAccessorFunction(_string) => Err((
                 MadeProgress,
-                Loc {
-                    region: loc_ident.region,
-                    value: Pattern::Malformed(string),
-                },
-                state,
+                EPattern::RecordAccessorFunction(loc_ident.region.start()),
+            )),
+            Ident::TupleAccessorFunction(_string) => Err((
+                MadeProgress,
+                EPattern::TupleAccessorFunction(loc_ident.region.start()),
             )),
             Ident::Malformed(malformed, problem) => {
                 debug_assert!(!malformed.is_empty());
diff --git a/crates/compiler/parse/src/string_literal.rs b/crates/compiler/parse/src/string_literal.rs
index 201ff6024d..325674f782 100644
--- a/crates/compiler/parse/src/string_literal.rs
+++ b/crates/compiler/parse/src/string_literal.rs
@@ -326,8 +326,12 @@ pub fn parse_str_like_literal<'a>() -> impl Parser<'a, StrLikeLiteral<'a>, EStri
 
                         if state.bytes().starts_with(b"\"\"\"") {
                             // ending the string; don't use the last newline
-                            segments
-                                .push(StrSegment::Plaintext(utf8(state.clone(), without_newline)?));
+                            if !without_newline.is_empty() {
+                                segments.push(StrSegment::Plaintext(utf8(
+                                    state.clone(),
+                                    without_newline,
+                                )?));
+                            }
                         } else {
                             segments
                                 .push(StrSegment::Plaintext(utf8(state.clone(), with_newline)?));
diff --git a/crates/compiler/parse/tests/test_parse.rs b/crates/compiler/parse/tests/test_parse.rs
index 0347aabce3..b22b7d7aa5 100644
--- a/crates/compiler/parse/tests/test_parse.rs
+++ b/crates/compiler/parse/tests/test_parse.rs
@@ -19,9 +19,9 @@ mod test_parse {
     use bumpalo::collections::vec::Vec;
     use bumpalo::{self, Bump};
     use roc_parse::ast::Expr::{self, *};
-    use roc_parse::ast::StrLiteral::*;
     use roc_parse::ast::StrSegment::*;
     use roc_parse::ast::{self, EscapedChar};
+    use roc_parse::ast::{CommentOrNewline, StrLiteral::*};
     use roc_parse::module::module_defs;
     use roc_parse::parser::{Parser, SyntaxError};
     use roc_parse::state::State;
@@ -322,6 +322,22 @@ mod test_parse {
         assert_eq!(std::mem::size_of::<roc_parse::ast::Expr>(), 40);
     }
 
+    #[test]
+    fn parse_two_line_comment_with_crlf() {
+        let src = "# foo\r\n# bar\r\n42";
+        assert_parses_to(
+            src,
+            Expr::SpaceBefore(
+                &Expr::Num("42"),
+                &[
+                    CommentOrNewline::LineComment(" foo"),
+                    // We used to have a bug where there was an extra CommentOrNewline::Newline between these.
+                    CommentOrNewline::LineComment(" bar"),
+                ],
+            ),
+        );
+    }
+
     // PARSE ERROR
 
     // TODO this should be parse error, but isn't!
diff --git a/crates/compiler/test_syntax/Cargo.toml b/crates/compiler/test_syntax/Cargo.toml
index e848124fed..513aea2d70 100644
--- a/crates/compiler/test_syntax/Cargo.toml
+++ b/crates/compiler/test_syntax/Cargo.toml
@@ -6,6 +6,9 @@ license = "UPL-1.0"
 edition = "2021"
 description = "Tests for the parse + fmt crates."
 
+[features]
+"parse_debug_trace" = ["roc_parse/parse_debug_trace"]
+
 [dependencies]
 roc_collections = { path = "../collections" }
 roc_region = { path = "../region" }
diff --git a/crates/compiler/test_syntax/src/test_helpers.rs b/crates/compiler/test_syntax/src/test_helpers.rs
index 0af0e4f574..a9d35e9851 100644
--- a/crates/compiler/test_syntax/src/test_helpers.rs
+++ b/crates/compiler/test_syntax/src/test_helpers.rs
@@ -219,7 +219,7 @@ impl<'a> Input<'a> {
                 * * * AST after formatting:\n{:#?}\n\n",
                 self.as_str(),
                 output.as_ref().as_str(),
-                ast_normalized,
+                actual,
                 reparsed_ast_normalized
             );
         }
@@ -229,7 +229,10 @@ impl<'a> Input<'a> {
             let reformatted = reparsed_ast.format();
 
             if output != reformatted {
-                eprintln!("Formatting bug; formatting is not stable.\nOriginal code:\n{}\n\nFormatted code:\n{}\n\n", self.as_str(), output.as_ref().as_str());
+                eprintln!("Formatting bug; formatting is not stable.\nOriginal code:\n{}\n\nFormatted code:\n{}\n\nAST:\n{:#?}\n\n",
+                    self.as_str(),
+                    output.as_ref().as_str(),
+                    actual);
                 eprintln!("Reformatting the formatted code changed it again, as follows:\n\n");
 
                 assert_multiline_str_eq!(output.as_ref().as_str(), reformatted.as_ref().as_str());
diff --git a/crates/compiler/test_syntax/tests/snapshots/fail/when_outdented_branch.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/fail/when_outdented_branch.expr.result-ast
index 37a4d24789..3d9b09ae77 100644
--- a/crates/compiler/test_syntax/tests/snapshots/fail/when_outdented_branch.expr.result-ast
+++ b/crates/compiler/test_syntax/tests/snapshots/fail/when_outdented_branch.expr.result-ast
@@ -1 +1 @@
-Expr(BadExprEnd(@20), @0)
\ No newline at end of file
+Expr(BadExprEnd(@22), @0)
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.formatted.roc
new file mode 100644
index 0000000000..c1feee4538
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.formatted.roc
@@ -0,0 +1,3 @@
+f
+    -5
+    2
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.result-ast
new file mode 100644
index 0000000000..1fb8443efb
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.result-ast
@@ -0,0 +1,25 @@
+Apply(
+    @0-1 SpaceAfter(
+        Var {
+            module_name: "",
+            ident: "f",
+        },
+        [
+            Newline,
+        ],
+    ),
+    [
+        @2-4 Num(
+            "-5",
+        ),
+        @5-6 SpaceBefore(
+            Num(
+                "2",
+            ),
+            [
+                Newline,
+            ],
+        ),
+    ],
+    Space,
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.roc
new file mode 100644
index 0000000000..2f398535c7
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/call_with_newlines.expr.roc
@@ -0,0 +1,3 @@
+f
+-5
+2
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.formatted.roc
new file mode 100644
index 0000000000..25b06802b5
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.formatted.roc
@@ -0,0 +1,3 @@
+F : e #
+
+q
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.result-ast
new file mode 100644
index 0000000000..c389718463
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.result-ast
@@ -0,0 +1,42 @@
+Defs(
+    Defs {
+        tags: [
+            Index(0),
+        ],
+        regions: [
+            @0-3,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+        ],
+        spaces: [],
+        type_defs: [
+            Alias {
+                header: TypeHeader {
+                    name: @0-1 "F",
+                    vars: [],
+                },
+                ann: @2-3 BoundVariable(
+                    "e",
+                ),
+            },
+        ],
+        value_defs: [],
+    },
+    @7-8 SpaceBefore(
+        Var {
+            module_name: "",
+            ident: "q",
+        },
+        [
+            LineComment(
+                "",
+            ),
+            Newline,
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.roc
new file mode 100644
index 0000000000..e635941d68
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_annotation.expr.roc
@@ -0,0 +1,4 @@
+F:e#
+
+
+q
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.formatted.roc
new file mode 100644
index 0000000000..4f7a758688
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.formatted.roc
@@ -0,0 +1 @@
+i # abc
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.result-ast
new file mode 100644
index 0000000000..d4280e0b8b
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.result-ast
@@ -0,0 +1,13 @@
+ParensAround(
+    SpaceAfter(
+        Var {
+            module_name: "",
+            ident: "i",
+        },
+        [
+            LineComment(
+                "abc",
+            ),
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.roc
new file mode 100644
index 0000000000..5735bef0cf
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_expr_in_parens.expr.roc
@@ -0,0 +1,2 @@
+(i#abc
+)
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.formatted.roc
new file mode 100644
index 0000000000..878f99f997
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.formatted.roc
@@ -0,0 +1,4 @@
+Z #
+h
+ : a
+j
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.result-ast
new file mode 100644
index 0000000000..b776193c97
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.result-ast
@@ -0,0 +1,54 @@
+Defs(
+    Defs {
+        tags: [
+            Index(0),
+        ],
+        regions: [
+            @0-7,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+        ],
+        spaces: [],
+        type_defs: [
+            Alias {
+                header: TypeHeader {
+                    name: @0-1 "Z",
+                    vars: [
+                        @3-4 SpaceAfter(
+                            SpaceBefore(
+                                Identifier(
+                                    "h",
+                                ),
+                                [
+                                    LineComment(
+                                        "",
+                                    ),
+                                ],
+                            ),
+                            [
+                                Newline,
+                            ],
+                        ),
+                    ],
+                },
+                ann: @6-7 BoundVariable(
+                    "a",
+                ),
+            },
+        ],
+        value_defs: [],
+    },
+    @8-9 SpaceBefore(
+        Var {
+            module_name: "",
+            ident: "j",
+        },
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.roc
new file mode 100644
index 0000000000..3737e7a247
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_after_tag_in_def.expr.roc
@@ -0,0 +1,4 @@
+Z#
+h
+:a
+j
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.formatted.roc
new file mode 100644
index 0000000000..57bb3f2aa9
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.formatted.roc
@@ -0,0 +1,3 @@
+w #
+ : n
+Q
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.result-ast
new file mode 100644
index 0000000000..8c1a407e5d
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.result-ast
@@ -0,0 +1,43 @@
+Defs(
+    Defs {
+        tags: [
+            Index(2147483648),
+        ],
+        regions: [
+            @0-5,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+        ],
+        spaces: [],
+        type_defs: [],
+        value_defs: [
+            Annotation(
+                @0-1 SpaceAfter(
+                    Identifier(
+                        "w",
+                    ),
+                    [
+                        LineComment(
+                            "",
+                        ),
+                    ],
+                ),
+                @4-5 BoundVariable(
+                    "n",
+                ),
+            ),
+        ],
+    },
+    @6-7 SpaceBefore(
+        Tag(
+            "Q",
+        ),
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.roc
new file mode 100644
index 0000000000..57f16a558a
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_colon_def.expr.roc
@@ -0,0 +1,3 @@
+w#
+:n
+Q
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.formatted.roc
new file mode 100644
index 0000000000..c58f1a8f8d
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.formatted.roc
@@ -0,0 +1,3 @@
+t #
+ = 3
+e
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.result-ast
new file mode 100644
index 0000000000..4b2904695d
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.result-ast
@@ -0,0 +1,44 @@
+Defs(
+    Defs {
+        tags: [
+            Index(2147483648),
+        ],
+        regions: [
+            @0-5,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+        ],
+        spaces: [],
+        type_defs: [],
+        value_defs: [
+            Body(
+                @0-1 SpaceAfter(
+                    Identifier(
+                        "t",
+                    ),
+                    [
+                        LineComment(
+                            "",
+                        ),
+                    ],
+                ),
+                @4-5 Num(
+                    "3",
+                ),
+            ),
+        ],
+    },
+    @6-7 SpaceBefore(
+        Var {
+            module_name: "",
+            ident: "e",
+        },
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.roc
new file mode 100644
index 0000000000..9cfd7a6e2c
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/comment_before_equals_def.expr.roc
@@ -0,0 +1,3 @@
+t#
+=3
+e
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_indent_not_enough.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_indent_not_enough.expr.result-ast
index 514b7e0deb..c2135064d2 100644
--- a/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_indent_not_enough.expr.result-ast
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_indent_not_enough.expr.result-ast
@@ -16,8 +16,11 @@ Defs(
         type_defs: [],
         value_defs: [
             Body(
-                @0-7 Malformed(
+                @0-7 MalformedIdent(
                     "my_list",
+                    Underscore(
+                        @3,
+                    ),
                 ),
                 @10-58 List(
                     Collection {
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_same_indent_no_trailing_comma.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_same_indent_no_trailing_comma.expr.result-ast
index 1c7660b38f..3a7d3753bd 100644
--- a/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_same_indent_no_trailing_comma.expr.result-ast
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_same_indent_no_trailing_comma.expr.result-ast
@@ -16,8 +16,11 @@ Defs(
         type_defs: [],
         value_defs: [
             Body(
-                @0-7 Malformed(
+                @0-7 MalformedIdent(
                     "my_list",
+                    Underscore(
+                        @3,
+                    ),
                 ),
                 @10-26 List(
                     [
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_same_indent_with_trailing_comma.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_same_indent_with_trailing_comma.expr.result-ast
index 294546c42b..d1eb0b352d 100644
--- a/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_same_indent_with_trailing_comma.expr.result-ast
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/list_closing_same_indent_with_trailing_comma.expr.result-ast
@@ -16,8 +16,11 @@ Defs(
         type_defs: [],
         value_defs: [
             Body(
-                @0-7 Malformed(
+                @0-7 MalformedIdent(
                     "my_list",
+                    Underscore(
+                        @3,
+                    ),
                 ),
                 @10-27 List(
                     Collection {
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.formatted.roc
new file mode 100644
index 0000000000..43444cf382
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.formatted.roc
@@ -0,0 +1,2 @@
+(F 1), r <- a
+W
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.result-ast
new file mode 100644
index 0000000000..68eca7d599
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.result-ast
@@ -0,0 +1,29 @@
+Backpassing(
+    [
+        @0-3 Apply(
+            @0-1 Tag(
+                "F",
+            ),
+            [
+                @2-3 NumLiteral(
+                    "1",
+                ),
+            ],
+        ),
+        @5-6 Identifier(
+            "r",
+        ),
+    ],
+    @10-11 Var {
+        module_name: "",
+        ident: "a",
+    },
+    @12-13 SpaceBefore(
+        Tag(
+            "W",
+        ),
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.roc
new file mode 100644
index 0000000000..c8fea3186b
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/multi_backpassing_with_apply.expr.roc
@@ -0,0 +1,2 @@
+F 1, r <- a
+W
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.formatted.roc
new file mode 100644
index 0000000000..ef0c9d1063
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.formatted.roc
@@ -0,0 +1,4 @@
+e
+    """
+    "\"
+    """
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.result-ast
new file mode 100644
index 0000000000..16882ddfcc
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.result-ast
@@ -0,0 +1,23 @@
+Apply(
+    @0-1 Var {
+        module_name: "",
+        ident: "e",
+    },
+    [
+        @1-10 Str(
+            Block(
+                [
+                    [
+                        Plaintext(
+                            "\"",
+                        ),
+                        EscapedChar(
+                            DoubleQuote,
+                        ),
+                    ],
+                ],
+            ),
+        ),
+    ],
+    Space,
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.roc
new file mode 100644
index 0000000000..454c8c7c15
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/multiline_string_in_apply.expr.roc
@@ -0,0 +1 @@
+e""""\""""
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.formatted.roc
new file mode 100644
index 0000000000..f85e7a3632
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.formatted.roc
@@ -0,0 +1,3 @@
+!
+"""
+"""
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.result-ast
new file mode 100644
index 0000000000..5caf01d342
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.result-ast
@@ -0,0 +1,8 @@
+UnaryOp(
+    @1-7 Str(
+        Block(
+            [],
+        ),
+    ),
+    @0-1 Not,
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.roc
new file mode 100644
index 0000000000..b22950073b
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/negate_multiline_string.expr.roc
@@ -0,0 +1 @@
+!""""""
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.formatted.roc
new file mode 100644
index 0000000000..f5a66c8ca0
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.formatted.roc
@@ -0,0 +1,4 @@
+a = A
+    -g
+    a
+a
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.result-ast
new file mode 100644
index 0000000000..ef0b842ae7
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.result-ast
@@ -0,0 +1,58 @@
+Defs(
+    Defs {
+        tags: [
+            Index(2147483648),
+        ],
+        regions: [
+            @0-9,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+        ],
+        spaces: [],
+        type_defs: [],
+        value_defs: [
+            Body(
+                @0-1 Identifier(
+                    "a",
+                ),
+                @2-9 Apply(
+                    @2-3 SpaceAfter(
+                        Tag(
+                            "A",
+                        ),
+                        [
+                            Newline,
+                        ],
+                    ),
+                    [
+                        @5-7 UnaryOp(
+                            @6-7 Var {
+                                module_name: "",
+                                ident: "g",
+                            },
+                            @5-6 Negate,
+                        ),
+                        @8-9 Var {
+                            module_name: "",
+                            ident: "a",
+                        },
+                    ],
+                    Space,
+                ),
+            ),
+        ],
+    },
+    @10-11 SpaceBefore(
+        Var {
+            module_name: "",
+            ident: "a",
+        },
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.roc
new file mode 100644
index 0000000000..6c9453c2c5
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/negative_in_apply_def.expr.roc
@@ -0,0 +1,3 @@
+a=A
+ -g a
+a
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.formatted.roc
new file mode 100644
index 0000000000..1f29cd8a05
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.formatted.roc
@@ -0,0 +1,4 @@
+x =
+    a : n
+    4
+_
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.result-ast
new file mode 100644
index 0000000000..a016587f95
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.result-ast
@@ -0,0 +1,64 @@
+Defs(
+    Defs {
+        tags: [
+            Index(2147483648),
+        ],
+        regions: [
+            @0-7,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+        ],
+        spaces: [],
+        type_defs: [],
+        value_defs: [
+            Body(
+                @0-1 Identifier(
+                    "x",
+                ),
+                @2-7 Defs(
+                    Defs {
+                        tags: [
+                            Index(2147483648),
+                        ],
+                        regions: [
+                            @2-5,
+                        ],
+                        space_before: [
+                            Slice(start = 0, length = 0),
+                        ],
+                        space_after: [
+                            Slice(start = 0, length = 0),
+                        ],
+                        spaces: [],
+                        type_defs: [],
+                        value_defs: [
+                            Annotation(
+                                @2-3 Identifier(
+                                    "a",
+                                ),
+                                @4-5 BoundVariable(
+                                    "n",
+                                ),
+                            ),
+                        ],
+                    },
+                    @6-7 Num(
+                        "4",
+                    ),
+                ),
+            ),
+        ],
+    },
+    @8-9 SpaceBefore(
+        Underscore(
+            "",
+        ),
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.roc
new file mode 100644
index 0000000000..35709dbea4
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/nested_def_without_newline.expr.roc
@@ -0,0 +1,2 @@
+x=a:n 4
+_
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.formatted.roc
new file mode 100644
index 0000000000..8c7e5a667f
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.formatted.roc
@@ -0,0 +1 @@
+A
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.result-ast
new file mode 100644
index 0000000000..bb557e38b2
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.result-ast
@@ -0,0 +1,10 @@
+ParensAround(
+    SpaceBefore(
+        Tag(
+            "A",
+        ),
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.roc
new file mode 100644
index 0000000000..7335a9c933
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_after_paren.expr.roc
@@ -0,0 +1,2 @@
+(
+A)
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.formatted.roc
new file mode 100644
index 0000000000..6cec6ba227
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.formatted.roc
@@ -0,0 +1,5 @@
+7
+== (
+    Q : c
+    42
+)
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.result-ast
new file mode 100644
index 0000000000..4a401f61bb
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.result-ast
@@ -0,0 +1,49 @@
+BinOps(
+    [
+        (
+            @0-1 SpaceAfter(
+                Num(
+                    "7",
+                ),
+                [
+                    Newline,
+                ],
+            ),
+            @2-4 Equals,
+        ),
+    ],
+    @5-11 ParensAround(
+        Defs(
+            Defs {
+                tags: [
+                    Index(0),
+                ],
+                regions: [
+                    @5-8,
+                ],
+                space_before: [
+                    Slice(start = 0, length = 0),
+                ],
+                space_after: [
+                    Slice(start = 0, length = 0),
+                ],
+                spaces: [],
+                type_defs: [
+                    Alias {
+                        header: TypeHeader {
+                            name: @5-6 "Q",
+                            vars: [],
+                        },
+                        ann: @7-8 BoundVariable(
+                            "c",
+                        ),
+                    },
+                ],
+                value_defs: [],
+            },
+            @9-11 Num(
+                "42",
+            ),
+        ),
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.roc
new file mode 100644
index 0000000000..e9d72b7baa
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_before_operator_with_defs.expr.roc
@@ -0,0 +1,2 @@
+7
+==(Q:c 42)
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.formatted.roc
new file mode 100644
index 0000000000..08831cf13a
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.formatted.roc
@@ -0,0 +1,3 @@
+A : A
+    A
+p
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.result-ast
new file mode 100644
index 0000000000..727ea8ca75
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.result-ast
@@ -0,0 +1,51 @@
+Defs(
+    Defs {
+        tags: [
+            Index(0),
+        ],
+        regions: [
+            @0-6,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+        ],
+        spaces: [],
+        type_defs: [
+            Alias {
+                header: TypeHeader {
+                    name: @0-1 "A",
+                    vars: [],
+                },
+                ann: @2-6 Apply(
+                    "",
+                    "A",
+                    [
+                        @5-6 SpaceBefore(
+                            Apply(
+                                "",
+                                "A",
+                                [],
+                            ),
+                            [
+                                Newline,
+                            ],
+                        ),
+                    ],
+                ),
+            },
+        ],
+        value_defs: [],
+    },
+    @7-8 SpaceBefore(
+        Var {
+            module_name: "",
+            ident: "p",
+        },
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.roc
new file mode 100644
index 0000000000..57404655f4
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/newline_in_type_alias_application.expr.roc
@@ -0,0 +1,3 @@
+A:A
+ A
+p
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.formatted.roc
new file mode 100644
index 0000000000..4c6b2d5b7a
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.formatted.roc
@@ -0,0 +1,2 @@
+J : R
+n_p
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.result-ast
new file mode 100644
index 0000000000..83779d17ea
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.result-ast
@@ -0,0 +1,42 @@
+Defs(
+    Defs {
+        tags: [
+            Index(0),
+        ],
+        regions: [
+            @0-3,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+        ],
+        spaces: [],
+        type_defs: [
+            Alias {
+                header: TypeHeader {
+                    name: @0-1 "J",
+                    vars: [],
+                },
+                ann: @2-3 Apply(
+                    "",
+                    "R",
+                    [],
+                ),
+            },
+        ],
+        value_defs: [],
+    },
+    @5-8 SpaceBefore(
+        MalformedIdent(
+            "n_p",
+            Underscore(
+                @7,
+            ),
+        ),
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.roc
new file mode 100644
index 0000000000..fa050810cd
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/underscore_expr_in_def.expr.roc
@@ -0,0 +1,2 @@
+J:R
+ n_p
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.formatted.roc b/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.formatted.roc
new file mode 100644
index 0000000000..70896ecac0
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.formatted.roc
@@ -0,0 +1,3 @@
+a : F
+F : h
+abc
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.result-ast b/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.result-ast
new file mode 100644
index 0000000000..2c0e9ed088
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.result-ast
@@ -0,0 +1,55 @@
+Defs(
+    Defs {
+        tags: [
+            Index(2147483648),
+            Index(0),
+        ],
+        regions: [
+            @0-3,
+            @4-8,
+        ],
+        space_before: [
+            Slice(start = 0, length = 0),
+            Slice(start = 0, length = 1),
+        ],
+        space_after: [
+            Slice(start = 0, length = 0),
+            Slice(start = 1, length = 0),
+        ],
+        spaces: [
+            Newline,
+        ],
+        type_defs: [
+            Alias {
+                header: TypeHeader {
+                    name: @4-5 "F",
+                    vars: [],
+                },
+                ann: @7-8 BoundVariable(
+                    "h",
+                ),
+            },
+        ],
+        value_defs: [
+            Annotation(
+                @0-1 Identifier(
+                    "a",
+                ),
+                @2-3 Apply(
+                    "",
+                    "F",
+                    [],
+                ),
+            ),
+        ],
+    },
+    @9-12 SpaceBefore(
+        Var {
+            module_name: "",
+            ident: "abc",
+        },
+        [
+            Newline,
+        ],
+    ),
+)
diff --git a/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.roc b/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.roc
new file mode 100644
index 0000000000..64954926a9
--- /dev/null
+++ b/crates/compiler/test_syntax/tests/snapshots/pass/value_def_confusion.expr.roc
@@ -0,0 +1,4 @@
+a:F
+F
+:h
+abc
\ No newline at end of file
diff --git a/crates/compiler/test_syntax/tests/test_fmt.rs b/crates/compiler/test_syntax/tests/test_fmt.rs
index ac447849fa..c00627dcc8 100644
--- a/crates/compiler/test_syntax/tests/test_fmt.rs
+++ b/crates/compiler/test_syntax/tests/test_fmt.rs
@@ -213,7 +213,6 @@ mod test_fmt {
             indoc!(
                 r#"
                 x = 0 # comment
-
                 x
                 "#
             ),
@@ -1410,6 +1409,7 @@ mod test_fmt {
                 r#"
                 f = \x ->
                     # 1st
+
                     # 2nd
                     x
 
@@ -1693,6 +1693,7 @@ mod test_fmt {
             ),
         );
 
+        // TODO: do we want to override the user's intent like this?
         expr_formats_to(
             indoc!(
                 r#"
@@ -1821,6 +1822,7 @@ mod test_fmt {
             ),
         );
 
+        // TODO: do we want to override the user's intent like this?
         expr_formats_to(
             indoc!(
                 r#"
diff --git a/crates/compiler/test_syntax/tests/test_snapshots.rs b/crates/compiler/test_syntax/tests/test_snapshots.rs
index bcbae8ce03..cbe46cad68 100644
--- a/crates/compiler/test_syntax/tests/test_snapshots.rs
+++ b/crates/compiler/test_syntax/tests/test_snapshots.rs
@@ -252,9 +252,15 @@ mod test_snapshots {
         pass/basic_tuple.expr,
         pass/basic_var.expr,
         pass/bound_variable.expr,
+        pass/call_with_newlines.expr,
         pass/closure_with_underscores.expr,
+        pass/comment_after_annotation.expr,
         pass/comment_after_def.moduledefs,
+        pass/comment_after_expr_in_parens.expr,
         pass/comment_after_op.expr,
+        pass/comment_after_tag_in_def.expr,
+        pass/comment_before_colon_def.expr,
+        pass/comment_before_equals_def.expr,
         pass/comment_before_op.expr,
         pass/comment_inside_empty_list.expr,
         pass/comment_with_non_ascii.expr,
@@ -303,26 +309,34 @@ mod test_snapshots {
         pass/mixed_docs.expr,
         pass/module_def_newline.moduledefs,
         pass/multi_backpassing.expr,
+        pass/multi_backpassing_with_apply.expr,
         pass/multi_char_string.expr,
         pass/multiline_string.expr,
+        pass/multiline_string_in_apply.expr,
         pass/multiline_tuple_with_comments.expr,
         pass/multiline_type_signature.expr,
         pass/multiline_type_signature_with_comment.expr,
         pass/multiple_fields.expr,
         pass/multiple_operators.expr,
         pass/neg_inf_float.expr,
+        pass/negate_multiline_string.expr,
         pass/negative_float.expr,
+        pass/negative_in_apply_def.expr,
         pass/negative_int.expr,
         pass/nested_def_annotation.moduledefs,
+        pass/nested_def_without_newline.expr,
         pass/nested_if.expr,
         pass/nested_module.header,
         pass/newline_after_equals.expr, // Regression test for https://github.com/roc-lang/roc/issues/51
         pass/newline_after_mul.expr,
+        pass/newline_after_paren.expr,
         pass/newline_after_sub.expr,
         pass/newline_and_spaces_before_less_than.expr,
         pass/newline_before_add.expr,
+        pass/newline_before_operator_with_defs.expr,
         pass/newline_before_sub.expr,
         pass/newline_in_packages.full,
+        pass/newline_in_type_alias_application.expr,
         pass/newline_in_type_def.expr,
         pass/newline_inside_empty_list.expr,
         pass/newline_singleton_list.expr,
@@ -407,7 +421,9 @@ mod test_snapshots {
         pass/unary_not.expr,
         pass/unary_not_with_parens.expr,
         pass/underscore_backpassing.expr,
+        pass/underscore_expr_in_def.expr,
         pass/underscore_in_assignment_pattern.expr,
+        pass/value_def_confusion.expr,
         pass/var_else.expr,
         pass/var_if.expr,
         pass/var_is.expr,