diff --git a/apps/generator/src/lib/deploy.ts b/apps/generator/src/lib/deploy.ts
index d719baf..74d66ee 100644
--- a/apps/generator/src/lib/deploy.ts
+++ b/apps/generator/src/lib/deploy.ts
@@ -104,12 +104,25 @@ export async function deployContainer(input: DeployInput): Promise<DeployHandle>
   });
 }
 
-export async function stopContainer(containerId: string): Promise<void> {
+export async function stopContainer(
+  containerId: string,
+): Promise<{ ok: boolean; detail: string }> {
+  if (!containerId || containerId.length < 4) {
+    return { ok: false, detail: 'invalid_container_id' };
+  }
   const { spawn } = await import('node:child_process');
-  await new Promise<void>((resolve) => {
-    const child = spawn('docker', ['rm', '-f', containerId], { stdio: 'ignore' });
-    child.on('close', () => resolve());
-    child.on('error', () => resolve());
+  return await new Promise<{ ok: boolean; detail: string }>((resolve) => {
+    const child = spawn('docker', ['rm', '-f', containerId], {
+      stdio: ['ignore', 'pipe', 'pipe'],
+    });
+    let err = '';
+    child.stderr?.on('data', (d: Buffer) => {
+      err += d.toString();
+    });
+    child.on('error', () => resolve({ ok: false, detail: 'spawn_failed' }));
+    child.on('close', (code) =>
+      resolve(code === 0 ? { ok: true, detail: '' } : { ok: false, detail: err.trim() || `exit ${code}` }),
+    );
   });
 }
 
diff --git a/apps/generator/src/worker.ts b/apps/generator/src/worker.ts
index ba0210e..f09904f 100644
--- a/apps/generator/src/worker.ts
+++ b/apps/generator/src/worker.ts
@@ -6,7 +6,7 @@ import { config } from './config.js';
 import { generateSpec } from './lib/claude.js';
 import { renderServerCode } from './lib/render.js';
 import { dockerBuild, prepareBuildContext, staticCheck } from './lib/build.js';
-import { allocatePort, deployContainer, dockerAvailable } from './lib/deploy.js';
+import { allocatePort, deployContainer, dockerAvailable, stopContainer } from './lib/deploy.js';
 import { emitDone, emitError, emitLog, emitStatus } from './lib/emit.js';
 
 const db = createDb();
@@ -46,6 +46,16 @@ export const worker = new Worker<JobData>(
     const { buildId, serverId, prompt, version, slug, secrets, previewId } = job.data;
     const log = (level: 'info' | 'warn' | 'error', msg: string) => emitLog(buildId, level, msg);
 
+    // Capture the container currently serving this server (if any) BEFORE the
+    // build mutates the row. On an iterate (version > 1) we deploy the new
+    // container, then tear this old one down — rolling-deploy, no orphan.
+    const [priorState] = await db
+      .select({ containerId: mcpServers.containerId })
+      .from(mcpServers)
+      .where(eq(mcpServers.id, serverId))
+      .limit(1);
+    const oldContainerId = priorState?.containerId ?? null;
+
     try {
       await db.update(builds).set({ status: 'generating', startedAt: new Date() }).where(eq(builds.id, buildId));
       await db.update(mcpServers).set({ status: 'generating', updatedAt: new Date() }).where(eq(mcpServers.id, serverId));
@@ -141,6 +151,18 @@ export const worker = new Worker<JobData>(
         .set({ status: 'live', currentVersion: version, publicUrl: handle.publicUrl, updatedAt: new Date() })
         .where(eq(mcpServers.id, serverId));
 
+      // Rolling deploy: the new container is live — now retire the previous one.
+      // Without this every iterate would leave an orphan holding a host port.
+      if (oldContainerId && oldContainerId !== handle.containerId) {
+        const stopped = await stopContainer(oldContainerId);
+        await log(
+          stopped.ok ? 'info' : 'warn',
+          stopped.ok
+            ? `Retired previous container ${oldContainerId.slice(0, 12)}`
+            : `Could not stop previous container ${oldContainerId.slice(0, 12)}: ${stopped.detail}`,
+        );
+      }
+
       await emitStatus(buildId, 'success');
       await emitDone(buildId, 'success', serverId, handle.publicUrl);
     } catch (err) {