diff --git a/.changeset/large-ears-ask.md b/.changeset/large-ears-ask.md
new file mode 100644
index 000000000000..d60878ca7066
--- /dev/null
+++ b/.changeset/large-ears-ask.md
@@ -0,0 +1,5 @@
+---
+'astro-vscode': patch
+---
+
+Fixes syntax highlighting sometimes not working when the frontmatter or script tags ended with certain TypeScript constructs
diff --git a/.vscode/launch.json b/.vscode/launch.json
index b575d4b70649..7aa3443bf9e4 100644
--- a/.vscode/launch.json
+++ b/.vscode/launch.json
@@ -7,16 +7,16 @@
       "type": "extensionHost",
       "request": "launch",
       "runtimeExecutable": "${execPath}",
-      "args": ["--extensionDevelopmentPath=${workspaceRoot}/tools/vscode"],
-      "outFiles": ["${workspaceRoot}/tools/vscode/dist/**/*.js"]
+      "args": ["--extensionDevelopmentPath=${workspaceRoot}/packages/language-tools/vscode"],
+      "outFiles": ["${workspaceRoot}/*/*/dist/**/*.js"]
     },
     {
+      "name": "Attach to Server",
       "type": "node",
       "request": "attach",
-      "name": "Attach to Server",
-      "port": 6040,
+      "port": 6009,
       "restart": true,
-      "outFiles": ["${workspaceRoot}/tools/languageserver/dist/**/*.js"],
+      "outFiles": ["${workspaceRoot}/*/*/dist/**/*.js"],
       "skipFiles": ["<node_internals>/**"]
     }
   ],
@@ -26,4 +26,4 @@
       "configurations": ["Launch Client", "Attach to Server"]
     }
   ]
-}
+}
\ No newline at end of file
diff --git a/packages/language-tools/vscode/syntaxes/astro.tmLanguage.json b/packages/language-tools/vscode/syntaxes/astro.tmLanguage.json
index 558c04d22fb7..d82f722e0096 100644
--- a/packages/language-tools/vscode/syntaxes/astro.tmLanguage.json
+++ b/packages/language-tools/vscode/syntaxes/astro.tmLanguage.json
@@ -1,7 +1,9 @@
 {
   "name": "Astro",
   "scopeName": "source.astro",
-  "fileTypes": ["astro"],
+  "fileTypes": [
+    "astro"
+  ],
   "injections": {
     "L:(meta.script.astro) (meta.lang.json) - (meta source)": {
       "patterns": [
@@ -20,9 +22,20 @@
     },
     "L:(meta.script.astro) (meta.lang.js | meta.lang.javascript | meta.lang.partytown | meta.lang.node) - (meta source)": {
       "patterns": [
+        {
+          "begin": "(?<=>)(?=[^\\n]+</script[\\s>])",
+          "end": "(?=</script[\\s>])",
+          "name": "meta.embedded.block.astro",
+          "contentName": "source.js",
+          "patterns": [
+            {
+              "include": "source.js"
+            }
+          ]
+        },
         {
           "begin": "(?<=>)(?!</)",
-          "end": "(?=</)",
+          "while": "^(?!\\s*</script[\\s>])",
           "name": "meta.embedded.block.astro",
           "contentName": "source.js",
           "patterns": [
@@ -35,9 +48,20 @@
     },
     "L:(meta.script.astro) (meta.lang.ts | meta.lang.typescript) - (meta source)": {
       "patterns": [
+        {
+          "begin": "(?<=>)(?=[^\\n]+</script[\\s>])",
+          "end": "(?=</script[\\s>])",
+          "name": "meta.embedded.block.astro",
+          "contentName": "source.ts",
+          "patterns": [
+            {
+              "include": "source.ts"
+            }
+          ]
+        },
         {
           "begin": "(?<=>)(?!</)",
-          "end": "(?=</)",
+          "while": "^(?!\\s*</script[\\s>])",
           "name": "meta.embedded.block.astro",
           "contentName": "source.ts",
           "patterns": [
@@ -50,9 +74,20 @@
     },
     "L:meta.script.astro - meta.lang - (meta source)": {
       "patterns": [
+        {
+          "begin": "(?<=>)(?=[^\\n]+</script[\\s>])",
+          "end": "(?=</script[\\s>])",
+          "name": "meta.embedded.block.astro",
+          "contentName": "source.js",
+          "patterns": [
+            {
+              "include": "source.js"
+            }
+          ]
+        },
         {
           "begin": "(?<=>)(?!</)",
-          "end": "(?=</)",
+          "while": "^(?!\\s*</script[\\s>])",
           "name": "meta.embedded.block.astro",
           "contentName": "source.js",
           "patterns": [
@@ -194,10 +229,28 @@
           "name": "comment"
         }
       },
-      "contentName": "source.ts",
       "patterns": [
         {
-          "include": "source.ts"
+          "begin": "(?<=\\n)(?=[^\\n]+^-{3})",
+          "end": "(?=^-{3})",
+          "name": "meta.embedded.block.astro",
+          "contentName": "source.ts",
+          "patterns": [
+            {
+              "include": "source.ts"
+            }
+          ]
+        },
+        {
+          "begin": "(?<=\\n)",
+          "while": "^(?!\\s*-{3})",
+          "name": "meta.embedded.block.astro",
+          "contentName": "source.ts",
+          "patterns": [
+            {
+              "include": "source.ts"
+            }
+          ]
         }
       ]
     },
@@ -841,4 +894,4 @@
       ]
     }
   }
-}
+}
\ No newline at end of file
diff --git a/packages/language-tools/vscode/syntaxes/astro.tmLanguage.src.yaml b/packages/language-tools/vscode/syntaxes/astro.tmLanguage.src.yaml
index 387e72624070..8ca69dd6138c 100644
--- a/packages/language-tools/vscode/syntaxes/astro.tmLanguage.src.yaml
+++ b/packages/language-tools/vscode/syntaxes/astro.tmLanguage.src.yaml
@@ -29,11 +29,17 @@ injections:
 
   # JavaScript | 'javascript' | 'source.js' | 'partytown'
   'L:(meta.script.astro) (meta.lang.js | meta.lang.javascript | meta.lang.partytown | meta.lang.node) - (meta source)':
-    patterns:
-      [
+    patterns: [
+        {
+          begin: '(?<=>)(?=[^\n]+</script[\s>])',
+          end: '(?=</script[\s>])',
+          name: meta.embedded.block.astro,
+          contentName: source.js,
+          patterns: [{ include: source.js }],
+        },
         {
           begin: '(?<=>)(?!</)',
-          end: '(?=</)',
+          while: '^(?!\s*</script[\s>])',
           name: meta.embedded.block.astro,
           contentName: source.js,
           patterns: [{ include: source.js }],
@@ -42,11 +48,17 @@ injections:
 
   # TypeScript | 'ts'
   'L:(meta.script.astro) (meta.lang.ts | meta.lang.typescript) - (meta source)':
-    patterns:
-      [
+    patterns: [
+        {
+          begin: '(?<=>)(?=[^\n]+</script[\s>])',
+          end: '(?=</script[\s>])',
+          name: meta.embedded.block.astro,
+          contentName: source.ts,
+          patterns: [{ include: source.ts }],
+        },
         {
           begin: '(?<=>)(?!</)',
-          end: '(?=</)',
+          while: '^(?!\s*</script[\s>])',
           name: meta.embedded.block.astro,
           contentName: source.ts,
           patterns: [{ include: source.ts }],
@@ -56,11 +68,17 @@ injections:
   # Script Languages
   # Default (JavaScript)
   'L:meta.script.astro - meta.lang - (meta source)':
-    patterns:
-      [
+    patterns: [
+        {
+          begin: '(?<=>)(?=[^\n]+</script[\s>])',
+          end: '(?=</script[\s>])',
+          name: meta.embedded.block.astro,
+          contentName: source.js,
+          patterns: [{ include: source.js }],
+        },
         {
           begin: '(?<=>)(?!</)',
-          end: '(?=</)',
+          while: '^(?!\s*</script[\s>])',
           name: meta.embedded.block.astro,
           contentName: source.js,
           patterns: [{ include: source.js }],
@@ -180,9 +198,22 @@ repository:
       1: { name: comment }
     endCaptures:
       2: { name: comment }
-    contentName: source.ts
-    patterns:
-      - include: source.ts
+    patterns: [
+        {
+          begin: '(?<=\n)(?=[^\n]+^-{3})',
+          end: '(?=^-{3})',
+          name: meta.embedded.block.astro,
+          contentName: source.ts,
+          patterns: [{ include: source.ts }],
+        },
+        {
+          begin: '(?<=\n)',
+          while: '^(?!\s*-{3})',
+          name: meta.embedded.block.astro,
+          contentName: source.ts,
+          patterns: [{ include: source.ts }],
+        },
+      ]
 
   # -------
   # SCOPE
diff --git a/packages/language-tools/vscode/test/grammar/fixtures/text.astro.snap b/packages/language-tools/vscode/test/grammar/fixtures/text.astro.snap
index bb904ba90cb3..7f137596491c 100644
--- a/packages/language-tools/vscode/test/grammar/fixtures/text.astro.snap
+++ b/packages/language-tools/vscode/test/grammar/fixtures/text.astro.snap
@@ -1,11 +1,11 @@
 >---
 #^^^ source.astro comment
 >const cool = "our frontmatter"
-#^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ source.astro source.ts
+#^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ source.astro meta.embedded.block.astro source.ts
 >console.log("Hello, World!")
-#^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ source.astro source.ts
+#^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ source.astro meta.embedded.block.astro source.ts
 >console.log(`This is ${cool}!`)
-#^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ source.astro source.ts
+#^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ source.astro meta.embedded.block.astro source.ts
 >---
 #^^^ source.astro comment
 >
diff --git a/packages/language-tools/vscode/test/grammar/fixtures/types-ending.astro b/packages/language-tools/vscode/test/grammar/fixtures/types-ending.astro
new file mode 100644
index 000000000000..df2c0eadc56a
--- /dev/null
+++ b/packages/language-tools/vscode/test/grammar/fixtures/types-ending.astro
@@ -0,0 +1,9 @@
+---
+type Something = "Hello"
+---
+
+<script>
+type Something = "Hello"
+</script>
+
+<div></div>
\ No newline at end of file
diff --git a/packages/language-tools/vscode/test/grammar/fixtures/types-ending.astro.snap b/packages/language-tools/vscode/test/grammar/fixtures/types-ending.astro.snap
new file mode 100644
index 000000000000..4ad4ff967c51
--- /dev/null
+++ b/packages/language-tools/vscode/test/grammar/fixtures/types-ending.astro.snap
@@ -0,0 +1,25 @@
+>---
+#^^^ source.astro comment
+>type Something = "Hello"
+#^^^^^^^^^^^^^^^^^^^^^^^^^ source.astro meta.embedded.block.astro source.ts
+>---
+#^^^ source.astro comment
+>
+><script>
+#^ source.astro meta.scope.tag.script.astro meta.script.astro meta.tag.start.astro punctuation.definition.tag.begin.astro
+# ^^^^^^ source.astro meta.scope.tag.script.astro meta.script.astro meta.tag.start.astro entity.name.tag.astro
+#       ^ source.astro meta.scope.tag.script.astro meta.script.astro meta.tag.start.astro punctuation.definition.tag.end.astro
+>type Something = "Hello"
+#^^^^^^^^^^^^^^^^^^^^^^^^^ source.astro meta.scope.tag.script.astro meta.script.astro meta.embedded.block.astro source.js
+></script>
+#^^ source.astro meta.scope.tag.script.astro meta.script.astro meta.tag.end.astro punctuation.definition.tag.begin.astro
+#  ^^^^^^ source.astro meta.scope.tag.script.astro meta.script.astro meta.tag.end.astro entity.name.tag.astro
+#        ^ source.astro meta.scope.tag.script.astro meta.script.astro meta.tag.end.astro punctuation.definition.tag.end.astro
+>
+><div></div>
+#^ source.astro meta.scope.tag.div.astro meta.tag.start.astro punctuation.definition.tag.begin.astro
+# ^^^ source.astro meta.scope.tag.div.astro meta.tag.start.astro entity.name.tag.astro
+#    ^ source.astro meta.scope.tag.div.astro meta.tag.start.astro punctuation.definition.tag.end.astro
+#     ^^ source.astro meta.scope.tag.div.astro meta.tag.end.astro punctuation.definition.tag.begin.astro
+#       ^^^ source.astro meta.scope.tag.div.astro meta.tag.end.astro entity.name.tag.astro
+#          ^ source.astro meta.scope.tag.div.astro meta.tag.end.astro punctuation.definition.tag.end.astro
\ No newline at end of file