diff --git a/cli/src/commands/docs/docs.ts b/cli/src/commands/docs/docs.ts
new file mode 100644
index 0000000000..288faf335d
--- /dev/null
+++ b/cli/src/commands/docs/docs.ts
@@ -0,0 +1,114 @@
+import { Command } from "@cliffy/command";
+import { colors } from "@cliffy/ansi/colors";
+import * as log from "../../core/log.ts";
+import { requireLogin } from "../../core/auth.ts";
+import { resolveWorkspace } from "../../core/context.ts";
+import { GlobalOptions } from "../../types.ts";
+
+interface DocContentItem {
+  title: string;
+  url: string;
+  source?: {
+    content?: Array<{ text: string }>;
+  };
+}
+
+interface InkeepResponse {
+  choices?: Array<{
+    message?: {
+      content?: string;
+    };
+  }>;
+}
+
+interface ParsedContent {
+  content?: DocContentItem[];
+}
+
+async function docs(
+  opts: GlobalOptions & { json?: boolean },
+  query: string
+) {
+  await requireLogin(opts);
+  const workspace = await resolveWorkspace(opts);
+
+  const url = `${workspace.remote}api/inkeep`;
+
+  console.log(colors.bold(`\nSearching Windmill docs...\n`));
+
+  let res: Response;
+  try {
+    res = await fetch(url, {
+      method: "POST",
+      headers: {
+        "Content-Type": "application/json",
+        Authorization: `Bearer ${workspace.token}`,
+      },
+      body: JSON.stringify({ query }),
+    });
+  } catch (e) {
+    throw new Error(`Network error connecting to ${workspace.remote}: ${e}`);
+  }
+
+  if (res.status === 403) {
+    log.info(
+      "Windmill documentation search is an Enterprise Edition feature. Please upgrade to use this command."
+    );
+    return;
+  }
+
+  if (!res.ok) {
+    throw new Error(
+      `Documentation search failed: ${res.status} ${res.statusText}\n${await res.text()}`
+    );
+  }
+
+  const data = (await res.json()) as InkeepResponse;
+  const raw = data.choices?.[0]?.message?.content;
+
+  if (!raw) {
+    log.info("No documentation found for this query.");
+    return;
+  }
+
+  let parsed: ParsedContent;
+  try {
+    parsed = JSON.parse(raw);
+  } catch {
+    throw new Error("Failed to parse documentation response.");
+  }
+
+  const items = parsed.content ?? [];
+
+  if (items.length === 0) {
+    log.info("No documentation found for this query.");
+    return;
+  }
+
+  if (opts.json) {
+    console.log(JSON.stringify(items, null, 2));
+    return;
+  }
+
+  for (const item of items) {
+    console.log(colors.bold(colors.cyan(`📄 ${item.title}`)));
+    if (item.url) {
+      console.log(`   ${colors.underline(item.url)}`);
+    }
+    const text = item.source?.content?.[0]?.text;
+    if (text) {
+      const snippet = text.length > 500 ? text.slice(0, 500) + "..." : text;
+      console.log(`   ${snippet}`);
+    }
+    console.log();
+  }
+}
+
+const command = new Command()
+  .name("docs")
+  .description("Search Windmill documentation. Requires Enterprise Edition.")
+  .arguments("<query:string>")
+  .option("--json", "Output results as JSON.")
+  .action(docs as any);
+
+export default command;
diff --git a/cli/src/main.ts b/cli/src/main.ts
index 65430cba2f..9f493ffff2 100755
--- a/cli/src/main.ts
+++ b/cli/src/main.ts
@@ -39,6 +39,7 @@ import queues from "./commands/queues/queues.ts";
 import dependencies from "./commands/dependencies/dependencies.ts";
 import init from "./commands/init/init.ts";
 import jobs from "./commands/jobs/jobs.ts";
+import docs from "./commands/docs/docs.ts";
 import { fetchVersion } from "./core/context.ts";
 
 export {
@@ -59,6 +60,7 @@ export {
   gitsyncSettings,
   instance,
   dev,
+  docs,
   hubPull,
   pull,
   push,
@@ -127,6 +129,7 @@ const command = new Command()
   .command("queues", queues)
   .command("dependencies", dependencies)
   .command("jobs", jobs)
+  .command("docs", docs)
   .command("version --version", "Show version information")
   .action(async (opts: any) => {
     console.log("CLI version: " + VERSION);