diff --git a/llamafile/high.cpp b/llamafile/high.cpp
index 9c2e9d78f0..3fe1cd0c48 100644
--- a/llamafile/high.cpp
+++ b/llamafile/high.cpp
@@ -48,40 +48,7 @@ static std::string extname(const std::string_view path) {
     return std::string(name.substr(dot_pos + 1));
 }
 
-int main(int argc, char *argv[]) {
-
-    // process flags
-    int opt;
-    int infd = 0;
-    int outfd = 1;
-    const char *lang = nullptr;
-    const char *inpath = nullptr;
-    while ((opt = getopt(argc, argv, "hl:o:")) != -1) {
-        switch (opt) {
-        case 'h':
-            printf("usage: %s [-l LANG] [-o OUTFILE] [INFILE]\n", argv[0]);
-            exit(0);
-        case 'l':
-            lang = optarg;
-            break;
-        case 'o':
-            if ((outfd = creat(optarg, 0644)) == -1) {
-                perror(optarg);
-                exit(1);
-            }
-            break;
-        default:
-            exit(1);
-        }
-    }
-    if (optind < argc) {
-        inpath = argv[optind];
-        if ((infd = open(inpath, O_RDONLY)) == -1) {
-            perror(inpath);
-            exit(1);
-        }
-    }
-
+static void highlight(int infd, int outfd, const char *lang, const char *inpath) {
     // create syntax highlighter
     Highlight *h;
     const char *ext;
@@ -123,3 +90,44 @@ int main(int argc, char *argv[]) {
     H.flush(&res);
     write(outfd, res.data(), res.size());
 }
+
+int main(int argc, char *argv[]) {
+
+    // process flags
+    int opt;
+    int outfd = 1;
+    const char *lang = nullptr;
+    while ((opt = getopt(argc, argv, "hl:o:")) != -1) {
+        switch (opt) {
+        case 'h':
+            printf("usage: %s [-l LANG] [-o OUTFILE] [INFILE]\n", argv[0]);
+            exit(0);
+        case 'l':
+            lang = optarg;
+            break;
+        case 'o':
+            if ((outfd = creat(optarg, 0644)) == -1) {
+                perror(optarg);
+                exit(1);
+            }
+            break;
+        default:
+            exit(1);
+        }
+    }
+
+    // process files
+    if (optind == argc) {
+        highlight(0, outfd, lang, 0);
+    } else {
+        for (int i = optind; i < argc; ++i) {
+            int infd;
+            const char *inpath = argv[i];
+            if ((infd = open(inpath, O_RDONLY)) == -1) {
+                perror(inpath);
+                exit(1);
+            }
+            highlight(infd, outfd, lang, inpath);
+        }
+    }
+}
diff --git a/llamafile/highlight.h b/llamafile/highlight.h
index 54d2e286fb..3595780890 100644
--- a/llamafile/highlight.h
+++ b/llamafile/highlight.h
@@ -471,8 +471,11 @@ class HighlightShell : public Highlight {
     int u_ = 0;
     int t_ = 0;
     int i_ = 0;
+    int curl_ = 0;
+    int last_ = 0;
     bool pending_heredoc_ = false;
     bool indented_heredoc_ = false;
+    bool no_interpolation_ = false;
     std::string word_;
     std::string heredoc_;
 };
diff --git a/llamafile/highlight_shell.cpp b/llamafile/highlight_shell.cpp
index 79ec29fcb8..b86e13a101 100644
--- a/llamafile/highlight_shell.cpp
+++ b/llamafile/highlight_shell.cpp
@@ -25,11 +25,17 @@ enum {
     WORD,
     QUOTE,
     DQUOTE,
+    DQUOTE_VAR,
+    DQUOTE_VAR2,
+    DQUOTE_CURL,
+    DQUOTE_CURL_BACKSLASH,
     DQUOTE_BACKSLASH,
     TICK,
     TICK_BACKSLASH,
     VAR,
     VAR2,
+    CURL,
+    CURL_BACKSLASH,
     COMMENT,
     LT,
     LT_LT,
@@ -37,6 +43,10 @@ enum {
     LT_LT_QNAME,
     HEREDOC_BOL,
     HEREDOC,
+    HEREDOC_VAR,
+    HEREDOC_VAR2,
+    HEREDOC_CURL,
+    HEREDOC_CURL_BACKSLASH,
     BACKSLASH,
 };
 
@@ -50,9 +60,10 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
     for (size_t i = 0; i < input.size(); ++i) {
         wchar_t c;
         int b = input[i] & 255;
+        last_ = c_;
         if (!u_) {
             if (b < 0300) {
-                c = b;
+                c_ = c = b;
             } else {
                 c_ = ThomPikeByte(b);
                 u_ = ThomPikeLen(b) - 1;
@@ -97,7 +108,7 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
             } else if (c == '<') {
                 t_ = LT;
                 *r += '<';
-            } else if (c == '#') {
+            } else if (c == '#' && (!last_ || isspace(last_))) {
                 *r += HI_COMMENT;
                 *r += '#';
                 t_ = COMMENT;
@@ -157,9 +168,10 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
                 t_ = NORMAL;
                 break;
             } else if (c == '{') {
-                append_wchar(r, c);
+                *r += '{';
                 *r += HI_VAR;
-                t_ = VAR2;
+                t_ = CURL;
+                curl_ = 1;
                 break;
             } else {
                 *r += HI_VAR;
@@ -177,6 +189,37 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
             }
             break;
 
+        case CURL:
+            if (c == '\\') {
+                t_ = CURL_BACKSLASH;
+                *r += HI_RESET;
+                *r += HI_ESCAPE;
+                *r += '\\';
+            } else if (c == '{') {
+                *r += HI_RESET;
+                *r += '{';
+                *r += HI_VAR;
+                ++curl_;
+            } else if (c == '}') {
+                *r += HI_RESET;
+                *r += '}';
+                if (!--curl_) {
+                    t_ = NORMAL;
+                }
+            } else if (ispunct(c)) {
+                *r += HI_RESET;
+                append_wchar(r, c);
+            } else {
+                append_wchar(r, c);
+            }
+            break;
+
+        case CURL_BACKSLASH:
+            append_wchar(r, c);
+            *r += HI_RESET;
+            t_ = CURL;
+            break;
+
         case COMMENT:
             append_wchar(r, c);
             if (c == '\n') {
@@ -193,13 +236,19 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
             }
             break;
 
+        Dquote:
         case DQUOTE:
-            append_wchar(r, c);
             if (c == '"') {
+                append_wchar(r, c);
                 *r += HI_RESET;
                 t_ = NORMAL;
             } else if (c == '\\') {
+                append_wchar(r, c);
                 t_ = DQUOTE_BACKSLASH;
+            } else if (c == '$') {
+                t_ = DQUOTE_VAR;
+            } else {
+                append_wchar(r, c);
             }
             break;
 
@@ -208,6 +257,73 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
             t_ = DQUOTE;
             break;
 
+        case DQUOTE_VAR:
+            if (c == '!' || //
+                c == '#' || //
+                c == '$' || //
+                c == '*' || //
+                c == '-' || //
+                c == '?' || //
+                c == '@' || //
+                c == '\\' || //
+                c == '^') {
+                *r += HI_BOLD;
+                *r += '$';
+                append_wchar(r, c);
+                *r += HI_UNBOLD;
+                t_ = DQUOTE;
+                break;
+            } else if (c == '{') {
+                *r += HI_BOLD;
+                *r += "${";
+                t_ = DQUOTE_CURL;
+                curl_ = 1;
+                break;
+            } else if (c == '(') {
+                *r += '$';
+                t_ = DQUOTE_VAR2;
+            } else {
+                *r += HI_BOLD;
+                *r += '$';
+                t_ = DQUOTE_VAR2;
+            }
+            // fallthrough
+
+        case DQUOTE_VAR2:
+            if (!isascii(c) || isalnum(c) || c == '_') {
+                append_wchar(r, c);
+            } else {
+                *r += HI_UNBOLD;
+                t_ = DQUOTE;
+                goto Dquote;
+            }
+            break;
+
+        case DQUOTE_CURL:
+            if (c == '\\') {
+                t_ = DQUOTE_CURL_BACKSLASH;
+                *r += '\\';
+            } else if (c == '{') {
+                *r += '{';
+                ++curl_;
+            } else if (c == '}') {
+                *r += '}';
+                if (!--curl_) {
+                    *r += HI_UNBOLD;
+                    t_ = DQUOTE;
+                }
+            } else if (ispunct(c)) {
+                append_wchar(r, c);
+            } else {
+                append_wchar(r, c);
+            }
+            break;
+
+        case DQUOTE_CURL_BACKSLASH:
+            append_wchar(r, c);
+            t_ = DQUOTE_CURL;
+            break;
+
         case TICK:
             append_wchar(r, c);
             if (c == '`') {
@@ -230,6 +346,7 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
                 heredoc_.clear();
                 pending_heredoc_ = false;
                 indented_heredoc_ = false;
+                no_interpolation_ = false;
             } else {
                 t_ = NORMAL;
                 goto Normal;
@@ -246,6 +363,7 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
                 t_ = LT_LT_QNAME;
                 *r += HI_STRING;
                 append_wchar(r, c);
+                no_interpolation_ = true;
             } else if (isalpha(c) || c == '_') {
                 t_ = LT_LT_NAME;
                 append_wchar(&heredoc_, c);
@@ -302,10 +420,83 @@ void HighlightShell::feed(std::string *r, std::string_view input) {
             }
             break;
 
+        Heredoc:
         case HEREDOC:
-            append_wchar(r, c);
-            if (c == '\n')
+            if (c == '\n') {
+                *r += '\n';
                 t_ = HEREDOC_BOL;
+            } else if (c == '$' && !no_interpolation_) {
+                t_ = HEREDOC_VAR;
+            } else {
+                append_wchar(r, c);
+            }
+            break;
+
+        case HEREDOC_VAR:
+            if (c == '!' || //
+                c == '#' || //
+                c == '$' || //
+                c == '*' || //
+                c == '-' || //
+                c == '?' || //
+                c == '@' || //
+                c == '\\' || //
+                c == '^') {
+                *r += HI_BOLD;
+                *r += '$';
+                append_wchar(r, c);
+                *r += HI_UNBOLD;
+                t_ = HEREDOC;
+                break;
+            } else if (c == '{') {
+                *r += HI_BOLD;
+                *r += "${";
+                t_ = HEREDOC_CURL;
+                curl_ = 1;
+                break;
+            } else if (c == '(') {
+                *r += '$';
+                t_ = HEREDOC_VAR2;
+            } else {
+                *r += HI_BOLD;
+                *r += '$';
+                t_ = HEREDOC_VAR2;
+            }
+            // fallthrough
+
+        case HEREDOC_VAR2:
+            if (!isascii(c) || isalnum(c) || c == '_') {
+                append_wchar(r, c);
+            } else {
+                *r += HI_UNBOLD;
+                t_ = HEREDOC;
+                goto Heredoc;
+            }
+            break;
+
+        case HEREDOC_CURL:
+            if (c == '\\') {
+                t_ = HEREDOC_CURL_BACKSLASH;
+                *r += '\\';
+            } else if (c == '{') {
+                *r += '{';
+                ++curl_;
+            } else if (c == '}') {
+                *r += '}';
+                if (!--curl_) {
+                    *r += HI_UNBOLD;
+                    t_ = HEREDOC;
+                }
+            } else if (ispunct(c)) {
+                append_wchar(r, c);
+            } else {
+                append_wchar(r, c);
+            }
+            break;
+
+        case HEREDOC_CURL_BACKSLASH:
+            append_wchar(r, c);
+            t_ = HEREDOC_CURL;
             break;
 
         default:
@@ -330,15 +521,31 @@ void HighlightShell::flush(std::string *r) {
         }
         word_.clear();
         break;
+    case DQUOTE_VAR:
+        *r += '$';
+        *r += HI_RESET;
+        break;
+    case HEREDOC_VAR:
+        *r += '$';
+        *r += HI_RESET;
+        break;
     case VAR2:
+    case CURL:
+    case CURL_BACKSLASH:
     case TICK:
     case TICK_BACKSLASH:
     case QUOTE:
     case DQUOTE:
+    case DQUOTE_VAR2:
+    case DQUOTE_CURL:
+    case DQUOTE_CURL_BACKSLASH:
     case DQUOTE_BACKSLASH:
     case COMMENT:
     case HEREDOC_BOL:
     case HEREDOC:
+    case HEREDOC_VAR2:
+    case HEREDOC_CURL:
+    case HEREDOC_CURL_BACKSLASH:
     case LT_LT_QNAME:
     case BACKSLASH:
         *r += HI_RESET;
@@ -349,4 +556,5 @@ void HighlightShell::flush(std::string *r) {
     c_ = 0;
     u_ = 0;
     t_ = NORMAL;
+    last_ = 0;
 }
diff --git a/llamafile/highlight_typescript.cpp b/llamafile/highlight_typescript.cpp
index 5680e76bfa..0bdde0be35 100644
--- a/llamafile/highlight_typescript.cpp
+++ b/llamafile/highlight_typescript.cpp
@@ -259,9 +259,9 @@ void HighlightTypescript::feed(std::string *r, std::string_view input) {
 
         case TICK_DOLLAR:
             if (c == '{' && nesti_ < sizeof(nest_)) {
-                // this is how the typescript playground highlights
-                *r += HI_RESET;
+                *r += HI_BOLD;
                 *r += '$';
+                *r += HI_UNBOLD;
                 *r += HI_STRING;
                 *r += '{';
                 *r += HI_RESET;
diff --git a/llamafile/is_keyword_typescript.gperf b/llamafile/is_keyword_typescript.gperf
index 99f7426db3..c9b3f30c47 100644
--- a/llamafile/is_keyword_typescript.gperf
+++ b/llamafile/is_keyword_typescript.gperf
@@ -54,6 +54,7 @@ set
 static
 switch
 target
+this
 throw
 try
 type