diff --git a/registry/coder/modules/code-server/main.tf b/registry/coder/modules/code-server/main.tf
index f56513533..4fc7e80e2 100644
--- a/registry/coder/modules/code-server/main.tf
+++ b/registry/coder/modules/code-server/main.tf
@@ -175,6 +175,7 @@ resource "coder_script" "code-server" {
     FOLDER : var.folder,
     AUTO_INSTALL_EXTENSIONS : var.auto_install_extensions,
     ADDITIONAL_ARGS : var.additional_args,
+    PARSE_JSONC_JS : file("${path.module}/parse_jsonc_extensions.js"),
   })
   run_on_start = true
 
diff --git a/registry/coder/modules/code-server/parse_jsonc_extensions.js b/registry/coder/modules/code-server/parse_jsonc_extensions.js
new file mode 100644
index 000000000..2efedbd45
--- /dev/null
+++ b/registry/coder/modules/code-server/parse_jsonc_extensions.js
@@ -0,0 +1,55 @@
+// Parses a JSONC file and prints extension recommendations, one per line.
+// Handles // comments, /* */ block comments (including multi-line), and trailing commas.
+// Used by code-server and vscode-web modules to parse .vscode/extensions.json
+// and .code-workspace files.
+//
+// Environment variables:
+//   FILE  - path to the JSONC file
+//   QUERY - jq-style query: "recommendations" (default) or "extensions.recommendations"
+var fs = require("fs");
+var text = fs.readFileSync(process.env.FILE, "utf8");
+var result = "";
+var inString = false;
+var i = 0;
+
+while (i < text.length) {
+  if (inString) {
+    if (text[i] === "\\" && i + 1 < text.length) {
+      result += text.slice(i, i + 2);
+      i += 2;
+      continue;
+    }
+    if (text[i] === '"') inString = false;
+    result += text[i++];
+  } else {
+    if (text[i] === '"') {
+      inString = true;
+      result += text[i++];
+      continue;
+    }
+    if (text[i] === "/" && text[i + 1] === "/") {
+      while (i < text.length && text[i] !== "\n") i++;
+      continue;
+    }
+    if (text[i] === "/" && text[i + 1] === "*") {
+      i += 2;
+      while (i < text.length && !(text[i] === "*" && text[i + 1] === "/")) i++;
+      i += 2;
+      continue;
+    }
+    result += text[i++];
+  }
+}
+
+result = result.replace(/,(\s*[\]}])/g, "$1");
+var data = JSON.parse(result);
+var query = process.env.QUERY || "recommendations";
+var recommendations;
+if (query === "extensions.recommendations") {
+  recommendations = (data.extensions && data.extensions.recommendations) || [];
+} else {
+  recommendations = data.recommendations || [];
+}
+recommendations.forEach(function (e) {
+  console.log(e);
+});
diff --git a/registry/coder/modules/code-server/parse_jsonc_extensions.test.ts b/registry/coder/modules/code-server/parse_jsonc_extensions.test.ts
new file mode 100644
index 000000000..71f86c366
--- /dev/null
+++ b/registry/coder/modules/code-server/parse_jsonc_extensions.test.ts
@@ -0,0 +1,70 @@
+import { describe, expect, it } from "bun:test";
+import { spawn, readableStreamToText } from "bun";
+import { unlink } from "node:fs/promises";
+import { join } from "node:path";
+
+const PARSER = join(import.meta.dir, "parse_jsonc_extensions.js");
+const TMP = join(import.meta.dir, "tmp_test.json");
+
+async function parseExtensions(
+  json: string,
+  query?: string,
+): Promise<string[]> {
+  await Bun.write(TMP, json);
+  try {
+    const proc = spawn([process.execPath, PARSER], {
+      env: { FILE: TMP, QUERY: query ?? "recommendations" },
+      stdout: "pipe",
+      stderr: "pipe",
+    });
+    const out = await readableStreamToText(proc.stdout);
+    const exitCode = await proc.exited;
+    if (exitCode !== 0) {
+      throw new Error(await readableStreamToText(proc.stderr));
+    }
+    return out.trim().split("\n").filter(Boolean);
+  } finally {
+    await unlink(TMP).catch(() => {});
+  }
+}
+
+describe("parse_jsonc_extensions", () => {
+  it("handles comments and trailing commas", async () => {
+    const result = await parseExtensions(`{
+      // line comment
+      "recommendations": [
+        "ms-python.python",
+        /* block comment */
+        "dbaeumer.vscode-eslint",  // inline
+      ],
+    }`);
+    expect(result).toEqual(["ms-python.python", "dbaeumer.vscode-eslint"]);
+  });
+
+  it("does not mangle URLs in strings", async () => {
+    const result = await parseExtensions(`{
+      "recommendations": [
+        "ms-python.python",
+        "https://example.com/custom.vsix"
+      ]
+    }`);
+    expect(result).toEqual([
+      "ms-python.python",
+      "https://example.com/custom.vsix",
+    ]);
+  });
+
+  it("handles .code-workspace format", async () => {
+    const result = await parseExtensions(
+      `{
+      "folders": [{"path": "."}],
+      "extensions": {
+        // Recommended
+        "recommendations": ["ms-python.python"],
+      },
+    }`,
+      "extensions.recommendations",
+    );
+    expect(result).toEqual(["ms-python.python"]);
+  });
+});
diff --git a/registry/coder/modules/code-server/run.sh b/registry/coder/modules/code-server/run.sh
index 33a6972a6..bf6c6271f 100644
--- a/registry/coder/modules/code-server/run.sh
+++ b/registry/coder/modules/code-server/run.sh
@@ -98,7 +98,8 @@ function extension_installed() {
   return 1
 }
 
-# Install each extension...
+# Install extensions...
+INSTALL_EXT_ARGS=()
 IFS=',' read -r -a EXTENSIONLIST <<< "$${EXTENSIONS}"
 # shellcheck disable=SC2066
 for extension in "$${EXTENSIONLIST[@]}"; do
@@ -109,19 +110,18 @@ for extension in "$${EXTENSIONLIST[@]}"; do
     continue
   fi
   printf "🧩 Installing extension $${CODE}$extension$${RESET}...\n"
-  output=$($CODE_SERVER "$EXTENSION_ARG" --force --install-extension "$extension")
+  INSTALL_EXT_ARGS+=(--install-extension "$extension")
+done
+# shellcheck disable=SC2170,SC2255
+if [ $${#INSTALL_EXT_ARGS[@]} -gt 0 ]; then
+  output=$($CODE_SERVER "$EXTENSION_ARG" --force "$${INSTALL_EXT_ARGS[@]}")
   if [ $? -ne 0 ]; then
-    echo "Failed to install extension: $extension: $output"
+    echo "Failed to install extensions: $output"
     exit 1
   fi
-done
+fi
 
 if [ "${AUTO_INSTALL_EXTENSIONS}" = true ]; then
-  if ! command -v jq > /dev/null; then
-    echo "jq is required to install extensions from a workspace file."
-    exit 0
-  fi
-
   WORKSPACE_DIR="$HOME"
   if [ -n "${FOLDER}" ]; then
     WORKSPACE_DIR="${FOLDER}"
@@ -129,14 +129,18 @@ if [ "${AUTO_INSTALL_EXTENSIONS}" = true ]; then
 
   if [ -f "$WORKSPACE_DIR/.vscode/extensions.json" ]; then
     printf "🧩 Installing extensions from %s/.vscode/extensions.json...\n" "$WORKSPACE_DIR"
-    # Use sed to remove single-line comments before parsing with jq
-    extensions=$(sed 's|//.*||g' "$WORKSPACE_DIR"/.vscode/extensions.json | jq -r '.recommendations[]')
+    extensions=$(FILE="$WORKSPACE_DIR/.vscode/extensions.json" "${INSTALL_PREFIX}/lib/node" -e '${PARSE_JSONC_JS}')
+    INSTALL_EXT_ARGS=()
     for extension in $extensions; do
       if extension_installed "$extension"; then
         continue
       fi
-      $CODE_SERVER "$EXTENSION_ARG" --force --install-extension "$extension"
+      INSTALL_EXT_ARGS+=(--install-extension "$extension")
     done
+    # shellcheck disable=SC2170,SC2255
+    if [ $${#INSTALL_EXT_ARGS[@]} -gt 0 ]; then
+      $CODE_SERVER "$EXTENSION_ARG" --force "$${INSTALL_EXT_ARGS[@]}"
+    fi
   fi
 fi
 
diff --git a/registry/coder/modules/vscode-web/main.tf b/registry/coder/modules/vscode-web/main.tf
index 7a2029c87..7af3d0852 100644
--- a/registry/coder/modules/vscode-web/main.tf
+++ b/registry/coder/modules/vscode-web/main.tf
@@ -186,6 +186,7 @@ resource "coder_script" "vscode-web" {
     FOLDER : var.folder,
     WORKSPACE : var.workspace,
     AUTO_INSTALL_EXTENSIONS : var.auto_install_extensions,
+    PARSE_JSONC_JS : file("${path.module}/parse_jsonc_extensions.js"),
     SERVER_BASE_PATH : local.server_base_path,
     COMMIT_ID : var.commit_id,
     PLATFORM : var.platform,
diff --git a/registry/coder/modules/vscode-web/parse_jsonc_extensions.js b/registry/coder/modules/vscode-web/parse_jsonc_extensions.js
new file mode 100644
index 000000000..2efedbd45
--- /dev/null
+++ b/registry/coder/modules/vscode-web/parse_jsonc_extensions.js
@@ -0,0 +1,55 @@
+// Parses a JSONC file and prints extension recommendations, one per line.
+// Handles // comments, /* */ block comments (including multi-line), and trailing commas.
+// Used by code-server and vscode-web modules to parse .vscode/extensions.json
+// and .code-workspace files.
+//
+// Environment variables:
+//   FILE  - path to the JSONC file
+//   QUERY - jq-style query: "recommendations" (default) or "extensions.recommendations"
+var fs = require("fs");
+var text = fs.readFileSync(process.env.FILE, "utf8");
+var result = "";
+var inString = false;
+var i = 0;
+
+while (i < text.length) {
+  if (inString) {
+    if (text[i] === "\\" && i + 1 < text.length) {
+      result += text.slice(i, i + 2);
+      i += 2;
+      continue;
+    }
+    if (text[i] === '"') inString = false;
+    result += text[i++];
+  } else {
+    if (text[i] === '"') {
+      inString = true;
+      result += text[i++];
+      continue;
+    }
+    if (text[i] === "/" && text[i + 1] === "/") {
+      while (i < text.length && text[i] !== "\n") i++;
+      continue;
+    }
+    if (text[i] === "/" && text[i + 1] === "*") {
+      i += 2;
+      while (i < text.length && !(text[i] === "*" && text[i + 1] === "/")) i++;
+      i += 2;
+      continue;
+    }
+    result += text[i++];
+  }
+}
+
+result = result.replace(/,(\s*[\]}])/g, "$1");
+var data = JSON.parse(result);
+var query = process.env.QUERY || "recommendations";
+var recommendations;
+if (query === "extensions.recommendations") {
+  recommendations = (data.extensions && data.extensions.recommendations) || [];
+} else {
+  recommendations = data.recommendations || [];
+}
+recommendations.forEach(function (e) {
+  console.log(e);
+});
diff --git a/registry/coder/modules/vscode-web/run.sh b/registry/coder/modules/vscode-web/run.sh
index 57bb760f9..da60c4932 100644
--- a/registry/coder/modules/vscode-web/run.sh
+++ b/registry/coder/modules/vscode-web/run.sh
@@ -92,7 +92,8 @@ if [ $? -ne 0 ]; then
 fi
 printf "$${BOLD}VS Code Web has been installed.\n"
 
-# Install each extension...
+# Install extensions...
+INSTALL_EXT_ARGS=()
 IFS=',' read -r -a EXTENSIONLIST <<< "$${EXTENSIONS}"
 # shellcheck disable=SC2066
 for extension in "$${EXTENSIONLIST[@]}"; do
@@ -100,39 +101,45 @@ for extension in "$${EXTENSIONLIST[@]}"; do
     continue
   fi
   printf "🧩 Installing extension $${CODE}$extension$${RESET}...\n"
-  output=$($VSCODE_WEB "$EXTENSION_ARG" --install-extension "$extension" --force)
+  INSTALL_EXT_ARGS+=(--install-extension "$extension")
+done
+# shellcheck disable=SC2170,SC2255
+if [ $${#INSTALL_EXT_ARGS[@]} -gt 0 ]; then
+  output=$($VSCODE_WEB "$EXTENSION_ARG" --force "$${INSTALL_EXT_ARGS[@]}")
   if [ $? -ne 0 ]; then
-    echo "Failed to install extension: $extension: $output"
+    echo "Failed to install extensions: $output"
   fi
-done
+fi
 
 if [ "${AUTO_INSTALL_EXTENSIONS}" = true ]; then
-  if ! command -v jq > /dev/null; then
-    echo "jq is required to install extensions from a workspace file."
+  INSTALL_EXT_ARGS=()
+
+  # Prefer WORKSPACE if set and points to a .code-workspace file
+  if [ -n "${WORKSPACE}" ] && [ -f "${WORKSPACE}" ]; then
+    printf "🧩 Installing extensions from %s...\n" "${WORKSPACE}"
+    extensions=$(FILE="${WORKSPACE}" QUERY="extensions.recommendations" "${INSTALL_PREFIX}/node" -e '${PARSE_JSONC_JS}')
+    for extension in $extensions; do
+      INSTALL_EXT_ARGS+=(--install-extension "$extension")
+    done
   else
-    # Prefer WORKSPACE if set and points to a file
-    if [ -n "${WORKSPACE}" ] && [ -f "${WORKSPACE}" ]; then
-      printf "🧩 Installing extensions from %s...\n" "${WORKSPACE}"
-      # Strip single-line comments then parse .extensions.recommendations[]
-      extensions=$(sed 's|//.*||g' "${WORKSPACE}" | jq -r '(.extensions.recommendations // [])[]')
+    # Fallback to folder-based .vscode/extensions.json (existing behavior)
+    WORKSPACE_DIR="$HOME"
+    if [ -n "${FOLDER}" ]; then
+      WORKSPACE_DIR="${FOLDER}"
+    fi
+    if [ -f "$WORKSPACE_DIR/.vscode/extensions.json" ]; then
+      printf "🧩 Installing extensions from %s/.vscode/extensions.json...\n" "$WORKSPACE_DIR"
+      extensions=$(FILE="$WORKSPACE_DIR/.vscode/extensions.json" "${INSTALL_PREFIX}/node" -e '${PARSE_JSONC_JS}')
       for extension in $extensions; do
-        $VSCODE_WEB "$EXTENSION_ARG" --install-extension "$extension" --force
+        INSTALL_EXT_ARGS+=(--install-extension "$extension")
       done
-    else
-      # Fallback to folder-based .vscode/extensions.json (existing behavior)
-      WORKSPACE_DIR="$HOME"
-      if [ -n "${FOLDER}" ]; then
-        WORKSPACE_DIR="${FOLDER}"
-      fi
-      if [ -f "$WORKSPACE_DIR/.vscode/extensions.json" ]; then
-        printf "🧩 Installing extensions from %s/.vscode/extensions.json...\n" "$WORKSPACE_DIR"
-        extensions=$(sed 's|//.*||g' "$WORKSPACE_DIR/.vscode/extensions.json" | jq -r '.recommendations[]')
-        for extension in $extensions; do
-          $VSCODE_WEB "$EXTENSION_ARG" --install-extension "$extension" --force
-        done
-      fi
     fi
   fi
+
+  # shellcheck disable=SC2170,SC2255
+  if [ $${#INSTALL_EXT_ARGS[@]} -gt 0 ]; then
+    $VSCODE_WEB "$EXTENSION_ARG" --force "$${INSTALL_EXT_ARGS[@]}"
+  fi
 fi
 
 run_vscode_web