diff --git a/integrations/code/package.json b/integrations/code/package.json
index 534974f..c5cfbd2 100644
--- a/integrations/code/package.json
+++ b/integrations/code/package.json
@@ -49,7 +49,9 @@
     "vscode": "^1.100.0"
   },
   "activationEvents": [
-    "onLanguage:python-markdown"
+    "onLanguage:python-markdown",
+    "workspaceContains:**/mkdocs.yml",
+    "workspaceContains:**/zensical.toml"
   ],
   "contributes": {
     "configurationDefaults": {
diff --git a/integrations/code/src/extension.ts b/integrations/code/src/extension.ts
index e4ba35a..5e3eeb2 100644
--- a/integrations/code/src/extension.ts
+++ b/integrations/code/src/extension.ts
@@ -24,6 +24,7 @@ import type { ExtensionContext } from "vscode";
 import type { LanguageClient } from "vscode-languageclient/node";
 
 import { registerCommands } from "./commands";
+import { promptFileAssociation } from "./extension/association";
 import { createLanguageClient } from "./extension/client";
 import { Context } from "./extension/context";
 import { getStudio } from "./extension/studio";
@@ -53,6 +54,9 @@ export async function activate(extension: ExtensionContext): Promise<void> {
     return;
   }
 
+  // Prompt user to associate Markdown files with Zensical Studio
+  await promptFileAssociation(context);
+
   // Register commands
   registerCommands(extension);
 
diff --git a/integrations/code/src/extension/association.ts b/integrations/code/src/extension/association.ts
new file mode 100644
index 0000000..9e5244b
--- /dev/null
+++ b/integrations/code/src/extension/association.ts
@@ -0,0 +1,144 @@
+/*
+ * Copyright (c) 2026 Zensical and contributors
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy
+ * of this software and associated documentation files (the "Software"), to
+ * deal in the Software without restriction, including without limitation the
+ * rights to use, copy, modify, merge, publish, distribute, sublicense, and/or
+ * sell copies of the Software, and to permit persons to whom the Software is
+ * furnished to do so, subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in
+ * all copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+ * FITNESS FOR A PARTICULAR PURPOSE AND NON-INFRINGEMENT. IN NO EVENT SHALL THE
+ * AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+ * LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING
+ * FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS
+ * IN THE SOFTWARE.
+ */
+
+import * as vscode from "vscode";
+import { basename } from "node:path";
+
+import type { Context } from "./context";
+
+/* ----------------------------------------------------------------------------
+ * Types
+ * ------------------------------------------------------------------------- */
+
+/**
+ * Project type.
+ */
+type Project = "MkDocs" | "Zensical";
+
+/* ----------------------------------------------------------------------------
+ * Functions
+ * ------------------------------------------------------------------------- */
+
+/**
+ * Prompt to associate Markdown files with Python Markdown.
+ *
+ * @param context - Extension context
+ */
+export async function promptFileAssociation(context: Context): Promise<void> {
+  const folders = vscode.workspace.workspaceFolders ?? [];
+  if (folders.length !== 1) {
+    return;
+  }
+
+  // If we have a single workspace folder, check if it contains a project
+  const [folder] = folders;
+  const project = await findProject(folder);
+  if (typeof project === "undefined") {
+    return;
+  }
+
+  // Check, if we already prompted the user for this workspace
+  const key = `association:${folder.uri.toString()}`;
+  if (context.getState<boolean>(key) === true) {
+    return;
+  }
+
+  // Check, if we already have an association for Markdown files to the
+  // Python Markdown grammar in this workspace, and if so, skip
+  const config = vscode.workspace.getConfiguration("files");
+  const effective = config.get<Record<string, string>>("associations") ?? {};
+  if (effective["*.md"] === "python-markdown") {
+    context.setState(key, true);
+    return;
+  }
+
+  // Prompt the user to associate Markdown files with Python Markdown
+  const result = await vscode.window.showInformationMessage(
+    `Detected ${project} project. ` +
+      `Associate Markdown files in '${folder.name}' with Python Markdown?`,
+    "Yes",
+    "Not now",
+  );
+
+  // If the user dismissed the prompt, don't ask again
+  if (typeof result === "undefined") {
+    return;
+  }
+
+  if (result !== "Yes") {
+    context.setState(key, true);
+    return;
+  }
+
+  // Update file associations for this workspace
+  const associations =
+    config.inspect<Record<string, string>>("associations")?.workspaceValue ??
+    {};
+  try {
+    await config.update(
+      "associations",
+      {
+        ...associations,
+        "*.md": "python-markdown",
+      },
+      vscode.ConfigurationTarget.Workspace,
+    );
+    context.setState(key, true);
+  } catch (error) {
+    const message = error instanceof Error ? error.message : String(error);
+    context.log(
+      `Failed to update file associations for '${folder.name}': ${message}`,
+    );
+  }
+}
+
+/* ----------------------------------------------------------------------------
+ * Helper functions
+ * ------------------------------------------------------------------------- */
+
+/**
+ * Return the first matching project type in a workspace folder.
+ *
+ * @param folder - Workspace folder
+ *
+ * @returns Project type or nothing
+ */
+async function findProject(
+  folder: vscode.WorkspaceFolder,
+): Promise<Project | undefined> {
+  const [match] = await vscode.workspace.findFiles(
+    new vscode.RelativePattern(folder, "**/{mkdocs.yml,zensical.toml}"),
+    null,
+    1,
+  );
+
+  // Return the project type based on the matching file name
+  switch (basename(match?.fsPath ?? "")) {
+    case "zensical.toml":
+      return "Zensical";
+    case "mkdocs.yml":
+      return "MkDocs";
+  }
+
+  // No matching project type found
+  return;
+}