diff --git a/leo/cli.rs b/leo/cli.rs
index 5a4a0d8e53..5393d0cc66 100644
--- a/leo/cli.rs
+++ b/leo/cli.rs
@@ -33,7 +33,13 @@ pub trait CLI {
     fn new<'a, 'b>() -> App<'a, 'b> {
         let arguments = &Self::ARGUMENTS
             .iter()
-            .map(|a| Arg::with_name(a.0).help(a.1).required(a.2).index(a.3))
+            .map(|a| {
+                let mut args = Arg::with_name(a.0).help(a.1).required(a.3).index(a.4);
+                if a.2.len() > 0 {
+                    args = args.possible_values(a.2);
+                }
+                args
+            })
             .collect::<Vec<Arg<'static, 'static>>>();
         let flags = &Self::FLAGS
             .iter()
@@ -56,7 +62,13 @@ pub trait CLI {
                     .about(s.1)
                     .args(
                         &s.2.iter()
-                            .map(|a| Arg::with_name(a.0).help(a.1).required(a.2).index(a.3))
+                            .map(|a| {
+                                let mut args = Arg::with_name(a.0).help(a.1).required(a.3).index(a.4);
+                                if a.2.len() > 0 {
+                                    args = args.possible_values(a.2);
+                                }
+                                args
+                            })
                             .collect::<Vec<Arg<'static, 'static>>>(),
                     )
                     .args(
diff --git a/leo/cli_types.rs b/leo/cli_types.rs
index 77e6085218..a2527635e7 100644
--- a/leo/cli_types.rs
+++ b/leo/cli_types.rs
@@ -24,9 +24,11 @@ pub type DescriptionType = &'static str;
 
 pub type RequiredType = bool;
 
+pub type PossibleValuesType = &'static [&'static str];
+
 pub type IndexType = u64;
 
-pub type ArgumentType = (NameType, DescriptionType, RequiredType, IndexType);
+pub type ArgumentType = (NameType, DescriptionType, PossibleValuesType, RequiredType, IndexType);
 
 // Format
 // "[flag] -f --flag 'Add flag description here'"
diff --git a/leo/commands/add.rs b/leo/commands/add.rs
index ca1d45a7fc..76084dfdcb 100644
--- a/leo/commands/add.rs
+++ b/leo/commands/add.rs
@@ -51,6 +51,7 @@ impl CLI for AddCommand {
         (
             "REMOTE",
             "Install a package from the Aleo Package Manager with the given remote",
+            &[],
             false,
             1u64,
         ),
diff --git a/leo/commands/login.rs b/leo/commands/login.rs
index 4c6b038598..01da218e0e 100644
--- a/leo/commands/login.rs
+++ b/leo/commands/login.rs
@@ -46,6 +46,7 @@ impl CLI for LoginCommand {
         (
             "NAME",
             "Sets the authentication token for login to the package manager",
+            &[],
             false,
             1u64,
         ),
diff --git a/leo/commands/new.rs b/leo/commands/new.rs
index d210ff6ebd..033b23186f 100644
--- a/leo/commands/new.rs
+++ b/leo/commands/new.rs
@@ -37,6 +37,7 @@ impl CLI for NewCommand {
         (
             "NAME",
             "Sets the resulting package name, defaults to the directory name",
+            &[],
             true,
             1u64,
         ),
diff --git a/leo/commands/remove.rs b/leo/commands/remove.rs
index 4b26ba3e9e..179d1b57a7 100644
--- a/leo/commands/remove.rs
+++ b/leo/commands/remove.rs
@@ -30,7 +30,13 @@ impl CLI for RemoveCommand {
     const ABOUT: AboutType = "Uninstall a package from the current package";
     const ARGUMENTS: &'static [ArgumentType] = &[
         // (name, description, required, index)
-        ("NAME", "Removes the package from the current directory", true, 1u64),
+        (
+            "NAME",
+            "Removes the package from the current directory",
+            &[],
+            true,
+            1u64,
+        ),
     ];
     const FLAGS: &'static [FlagType] = &[];
     const NAME: NameType = "remove";
diff --git a/leo/commands/update.rs b/leo/commands/update.rs
index 12df354418..fb4c712d34 100644
--- a/leo/commands/update.rs
+++ b/leo/commands/update.rs
@@ -133,12 +133,13 @@ impl CLI for UpdateAutomatic {
         // (name, description, required, index)
         (
             "automatic",
-            "Enable or disable automatic updates [possible values: true, false]",
+            "Enable or disable automatic updates",
+            &["true", "false"],
             false,
             1u64,
         ),
     ];
-    const FLAGS: &'static [FlagType] = &[("--quiet")];
+    const FLAGS: &'static [FlagType] = &["[quiet] -q --quiet 'Suppress outputs to terminal'"];
     const NAME: NameType = "automatic";
     const OPTIONS: &'static [OptionType] = &[];
     const SUBCOMMANDS: &'static [SubCommandType] = &[];
@@ -152,11 +153,7 @@ impl CLI for UpdateAutomatic {
                 let automatic = match automatic {
                     "true" => Some(true),
                     "false" => Some(false),
-                    _ => {
-                        // TODO (raychu86) fix this log output
-                        tracing::info!("Possible values for this flag are `true` or `false`.");
-                        None
-                    }
+                    _ => unreachable!(),
                 };
 
                 Ok((automatic, quiet))