diff --git a/rc/filetype/pony.kak b/rc/filetype/pony.kak
index f0fa8e284..6a91688be 100644
--- a/rc/filetype/pony.kak
+++ b/rc/filetype/pony.kak
@@ -16,10 +16,12 @@ hook global WinSetOption filetype=pony %{
 
     set-option window static_words %opt{pony_static_words}
 
-    hook window InsertChar \n -group pony-insert pony-insert-on-new-line
-    hook window InsertChar \n -group pony-indent pony-indent-on-new-line
     # cleanup trailing whitespaces on current line insert end
     hook window ModeChange pop:insert:.* -group pony-trim-indent %{ try %{ execute-keys -draft <semicolon> x s ^\h+$ <ret> d } }
+    hook window InsertChar \n -group pony-indent pony-indent-on-new-line
+    hook window InsertChar \n -group pony-insert pony-insert-on-new-line
+
+    set-option buffer extra_word_chars '_' "'"
 
     hook -once -always window WinSetOption filetype=.* %{ remove-hooks window pony-.+ }
 }
@@ -29,47 +31,78 @@ hook -group pony-highlight global WinSetOption filetype=pony %{
     hook -once -always window WinSetOption filetype=.* %{ remove-highlighter pony }
 }
 
-provide-module pony %{
+provide-module pony %§
 
 # Highlighters & Completion
 # ‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾‾
 
 add-highlighter shared/pony regions
 add-highlighter shared/pony/code default-region group
-add-highlighter shared/pony/triple_string region '"""' '"""'            fill string
-add-highlighter shared/pony/double_string region '"'   (?<!\\)(\\\\)*"  fill string
-add-highlighter shared/pony/comment       region '/\*'   '\*/'          fill comment
-add-highlighter shared/pony/line_comment  region '//'   '$'             fill comment
 
+add-highlighter shared/pony/comment region '/\*' '\*/' fill comment
+add-highlighter shared/pony/line_comment region '//' '$' fill comment
+
+# String literals
+add-highlighter shared/pony/string region -match-capture '("""|")' '(?<!\\)(?:\\\\)*("""|")' group
+add-highlighter shared/pony/string/ fill string
+add-highlighter shared/pony/string/ regex '(?:\\a|\\b|\\e|\\f|\\n|\\r|\\t||\\v|\\\\|\\''|\\0|\\x[0-9a-fA-F]{2}|\\u[0-9a-fA-F]{4}|\\u[0-9a-fA-F]{6})' 0:meta
+
+# Character literals
+# negative lookbehind to account for variables with prime such as myvar' or myvar''
+add-highlighter shared/pony/character region "(?<![a-z0-9'])'" (?<!\\)(\\\\)*' group
+add-highlighter shared/pony/character/ fill string
+add-highlighter shared/pony/character/ regex '(?:\\a|\\b|\\e|\\f|\\n|\\r|\\t||\\v|\\\\|\\''|\\0|\\x[0-9a-fA-F]{2})' 0:meta
+
+# Operators
+add-highlighter shared/pony/code/ regex '=|\+|-|\*|/|%|%%|<<|>>|==|!=|<|<=|>=|>|=>|;' 0:operator
+add-highlighter shared/pony/code/ regex '(\+|-|\*|/|%|%%|<<|>>|==|!=|<|<=|>=|>)~' 0:operator
+add-highlighter shared/pony/code/ regex '(\+|-|\*|/|%|%%)\?' 0:operator
+add-highlighter shared/pony/code/ regex '^\h*|' 0:operator
+add-highlighter shared/pony/code/ regex '\b_\b' 0:operator
+
+# Integer literals
+add-highlighter shared/pony/code/ regex '\b[0-9](_?[0-9])*\b' 0:value
+add-highlighter shared/pony/code/ regex '\b0x[0-9a-fA-F](_?[0-9a-fA-F])*\b' 0:value
+add-highlighter shared/pony/code/ regex '\b0b[01](_?[01])*\b' 0:value
+
+# Float literals
+add-highlighter shared/pony/code/ regex '\b[0-9]+\.[0-9]+(?:[eE][-+]?[0-9]+)?\b' 0:value
+add-highlighter shared/pony/code/ regex '\b[0-9]+[eE][-+]?[0-9]+\b' 0:value
+
+# Type literals
+add-highlighter shared/pony/code/ regex '\b_?[A-Z][A-Za-z0-9]*\b' 0:type
+
+# Literal words are highlighted below to also allow for autocompletion by appending
+# them to static_words.
 evaluate-commands %sh{
     # Grammar
-    values="true|false|None|this"
+    values="true|false|this"
     meta='use'
     # Keyword list is collected using `keyword.kwlist` from `keyword`
-    keywords="and|as|or|break|match|continue|else|try|in|return|end|for|is"
-    keywords="${keywords}|recover|consume|error|do|then|if|while"
-    func_decl="new|fun|be|lambda"
+    keywords="as|break|match|continue|else|elseif|try|in|return|end|for|is"
+    keywords="${keywords}|recover|consume|error|do|then|if|while|where|with"
+    keywords="${keywords}|class|struct|object|actor|interface|trait|primitive"
+    keywords="${keywords}|type|var|let|embed|repeat|until|addressof"
+    func_decl="new|fun|be"
     capabilities="iso|ref|box|tag|val|trn"
-    struct="class|actor|interface|trait|primitive|type|var|let|embed"
-
+    operators="and|or|xor|not"
+    builtin_types="String|None|Any|Array"
 
     # Add the language's grammar to the static completion list
     static_words="${values} ${meta} ${keywords} ${types_decl} ${capabilities}"
-    static_words="${static_words} ${struct}"
+    static_words="${static_words} ${operators} ${builtin_types}"
     printf %s\\n "declare-option str-list pony_static_words ${static_words}" | tr '|' ' '
 
     # Highlight keywords
+    # The (?!') ensures that keywords with prime are highlighted as usual, for example try'
     printf %s "
-        add-highlighter shared/pony/code/ regex '\b(${values})\b' 0:value
-        add-highlighter shared/pony/code/ regex '\b(${meta})\b' 0:meta
-        add-highlighter shared/pony/code/ regex '\b(${func_decl})(\s+(${capabilities}))?(\s+\w+)\(' 1:type 3:builtin 4:builtin
-        add-highlighter shared/pony/code/ regex '\b(${func_decl})\b' 0:type
-        add-highlighter shared/pony/code/ regex '=>' 0:type
-        add-highlighter shared/pony/code/ regex '\b(${keywords})\b' 0:keyword
-        add-highlighter shared/pony/code/ regex ';' 0:keyword
-        add-highlighter shared/pony/code/ regex '^\s*|' 0:keyword
-        add-highlighter shared/pony/code/ regex '\b(${struct})\b' 0:variable
-        add-highlighter shared/pony/code/ regex '\b(${capabilities})\b(!|^)?' 1:builtin 2:builtin
+        add-highlighter shared/pony/code/ regex \b(${values})\b(?!') 0:value
+        add-highlighter shared/pony/code/ regex \b(${operators})\b(?!') 0:operator
+        add-highlighter shared/pony/code/ regex \b(${meta})\b(?!') 0:meta
+        add-highlighter shared/pony/code/ regex \b(${func_decl})(\s+(${capabilities}))?(\s+\w+)[\[(] 1:keyword 3:attribute 4:function
+        add-highlighter shared/pony/code/ regex \b(${func_decl})\b(?!') 0:keyword
+        add-highlighter shared/pony/code/ regex \b(${keywords})\b(?!') 0:keyword
+        add-highlighter shared/pony/code/ regex \b(${capabilities})\b(?!')(!|\\^)? 1:attribute 2:attribute
     "
 
     # Highlight types and attributes
@@ -81,24 +114,42 @@ evaluate-commands %sh{
 # Commands
 # ‾‾‾‾‾‾‾‾
 
-define-command -hidden pony-insert-on-new-line %{
-    evaluate-commands -draft -itersel %{
+define-command -hidden pony-insert-on-new-line %<
+    evaluate-commands -no-hooks -draft -itersel %<
         # copy // comments prefix and following white spaces
-        try %{ execute-keys -draft k x s ^\h*//\h* <ret> y jgh P }
-    }
-}
+        try %{ execute-keys -draft k x s ^\h*\K//\h* <ret> y jgi P }
+
+        # wisely add `end` keyword
+        evaluate-commands -save-regs x %<
+            try %{ execute-keys -draft k x s ^ \h + <ret> \" x y } catch %{ reg x '' }
+            try %<
+                evaluate-commands -draft %<
+                    # Check if previous line opens a block
+                    execute-keys -draft kx <a-k>^<c-r>x(try|match|recover|repeat|object|.+\bdo$|.+\bthen$)[^0-9A-Za-z_']<ret>
+                    # Check that we didn't put an end on the previous line that closes the block
+                    execute-keys -draft kx <a-K> \bend$<ret>
+                    # Check that we do not already have an end for this indent level which is first set via `pony-indent-on-new-line` hook
+                    execute-keys -draft }i J x <a-K> ^<c-r>x(end|else|elseif|until)[^0-9A-Za-z_']<ret>
+                >
+                execute-keys -draft o<c-r>xend<esc> # insert a new line with containing end
+            >
+        >
+    >
+>
 
 define-command -hidden pony-indent-on-new-line %{
-    evaluate-commands -draft -itersel %{
+    evaluate-commands -no-hooks -draft -itersel %{
         # preserve previous line indent
         try %{ execute-keys -draft , K <a-&> }
         # cleanup trailing whitespaces from previous line
         try %{ execute-keys -draft k x s \h+$ <ret> d }
-        # indent after line ending with :
-        try %{ execute-keys -draft , k x <a-k> (\b(?:do|try|then|else)|:|=>)$ <ret> j <a-gt> }
+        # indent after line ending with: =>, do, try, then, else, =; or
+        # starting with: actor, class, struct, trait, interface, if, elseif, recover, repeat
+        # excluding: primitive, type -- because they are often written in a single line
+        try %{ execute-keys -draft , k x <a-k> (\b(?:do|try|then|else|recover|repeat)|=>|=)$ | ^\h*(actor|class|struct|trait|interface|object)\b <ret> j <a-gt> }
         # else, end are always de-indented
         try %{ execute-keys -draft , k x <a-k> \b(else|end):$ <ret> k x s ^\h* <ret> y j x <a-k> ^<c-r>" <ret> J <a-lt> }
     }
 }
 
-}
+§
diff --git a/rc/tools/comment.kak b/rc/tools/comment.kak
index 8ebe088f7..b61007311 100644
--- a/rc/tools/comment.kak
+++ b/rc/tools/comment.kak
@@ -16,7 +16,7 @@ hook global BufSetOption filetype=asciidoc %{
     set-option buffer comment_block_end '////'
 }
 
-hook global BufSetOption filetype=(c|cpp|dart|gluon|go|java|javascript|objc|odin|php|protobuf|rust|sass|scala|scss|swift|typescript|groovy) %{
+hook global BufSetOption filetype=(c|cpp|dart|gluon|go|java|javascript|objc|odin|php|pony|protobuf|rust|sass|scala|scss|swift|typescript|groovy) %{
     set-option buffer comment_line '//'
     set-option buffer comment_block_begin '/*'
     set-option buffer comment_block_end '*/'