diff --git a/packages/deploy-cloudflare/src/operations.ts b/packages/deploy-cloudflare/src/operations.ts
index be801e95f..c6ccb4b31 100644
--- a/packages/deploy-cloudflare/src/operations.ts
+++ b/packages/deploy-cloudflare/src/operations.ts
@@ -39,6 +39,7 @@ export type CloudflareOperation =
       type: 'versions.deploy';
       versions: Array<{ versionId: string; percentage: number }>;
       message?: string;
+      bypassDeploymentChecks?: boolean;
     } & WorkerTarget)
   | ({
       type: 'versions.upload' | 'worker.deploy';
diff --git a/packages/deploy-cloudflare/src/version.ts b/packages/deploy-cloudflare/src/version.ts
index c040b8706..3e37a4710 100644
--- a/packages/deploy-cloudflare/src/version.ts
+++ b/packages/deploy-cloudflare/src/version.ts
@@ -2534,7 +2534,7 @@ async function deployVersionPercentages(
   options: Pick<
     Parameters<typeof activateCloudflareVersion>[0],
     'runWrangler' | 'workerName' | 'preserveTriggers' | 'configPath'
-  >,
+  > & { bypassDeploymentChecks?: boolean },
   percentages: Array<string>,
   message: string,
 ): Promise<CloudflareCommandResult> {
@@ -2557,6 +2557,7 @@ async function deployVersionPercentages(
       configPath: options.configPath,
       workerName: options.workerName,
       message,
+      ...(options.bypassDeploymentChecks ? { bypassDeploymentChecks: true } : {}),
     },
     { capture: false },
   );
@@ -2569,6 +2570,7 @@ export async function deployCloudflareVersionTraffic(options: {
   workerName: string;
   percentages: Array<string>;
   message: string;
+  bypassDeploymentChecks?: boolean;
 }): Promise<CloudflareCommandResult> {
   const config = pickWranglerTriggerContext(parseRootWranglerConfig(options.configPath));
   const directory = mkdtempSync(join(tmpdir(), 'void-version-traffic-'));
@@ -2582,6 +2584,7 @@ export async function deployCloudflareVersionTraffic(options: {
         configPath: path,
         workerName: options.workerName,
         message: options.message,
+        ...(options.bypassDeploymentChecks ? { bypassDeploymentChecks: true } : {}),
       },
       { capture: false },
     );
@@ -2615,7 +2618,7 @@ async function restorePreviousVersion(
     return 'unsafe';
   }
   const result = await deployVersionPercentages(
-    options,
+    { ...options, bypassDeploymentChecks: true },
     [`${previousVersionId}@100`],
     `Void automatic rollback after ${cause}.`,
   );
diff --git a/packages/deploy-cloudflare/test/unit/operations.test.ts b/packages/deploy-cloudflare/test/unit/operations.test.ts
index 504277194..00e99526e 100644
--- a/packages/deploy-cloudflare/test/unit/operations.test.ts
+++ b/packages/deploy-cloudflare/test/unit/operations.test.ts
@@ -1,3 +1,6 @@
+import { mkdtempSync, rmSync, writeFileSync } from 'node:fs';
+import { tmpdir } from 'node:os';
+import { join } from 'node:path';
 import { expect, it, vi } from 'vite-plus/test';
 import type { CloudflareCommandResult, CloudflareCommandRunner } from '../../src/execute.ts';
 import type { CloudflareOperation } from '../../src/operations.ts';
@@ -6,9 +9,10 @@ import { activateCloudflareVersion, encodeCloudflareVersionMessage } from '../..
 const current = '11111111-1111-4111-8111-111111111111';
 const next = '22222222-2222-4222-8222-222222222222';
 
-function setup(data: unknown) {
+function setup(data: unknown, failure?: 'activation' | 'triggers') {
   const calls: Array<CloudflareOperation> = [];
   let uploaded = false;
+  let triggerFailed = false;
   let versions = [{ version_id: current, percentage: 100 }];
   const runWrangler: CloudflareCommandRunner = vi.fn((operation: CloudflareOperation) => {
     calls.push(operation);
@@ -22,17 +26,45 @@ function setup(data: unknown) {
       case 'deployments.status':
         return ok({ versions });
       case 'versions.list':
-        return ok([{ id: current, number: 1 }, ...(uploaded ? [{ id: next, number: 2 }] : [])]);
+        return ok([
+          {
+            id: current,
+            number: 1,
+            annotations: {
+              'workers/message': encodeCloudflareVersionMessage([], {
+                workers_dev: true,
+                preview_urls: true,
+                routes: [],
+                crons: ['0 * * * *'],
+                queueConsumers: [],
+                workflows: [],
+              }),
+            },
+          },
+          ...(uploaded ? [{ id: next, number: 2 }] : []),
+        ]);
       case 'versions.upload':
         uploaded = true;
         return ok(data);
       case 'versions.deploy':
+        if (
+          failure === 'activation' &&
+          operation.versions.some(
+            (version) => version.versionId === next && version.percentage === 100,
+          )
+        ) {
+          return { ...ok(), status: 1 };
+        }
         versions = operation.versions.map(({ versionId, percentage }) => ({
           version_id: versionId,
           percentage,
         }));
         return ok();
       case 'triggers.deploy':
+        if (failure === 'triggers' && !triggerFailed) {
+          triggerFailed = true;
+          return { ...ok(), status: 1 };
+        }
         return ok();
       default:
         throw new Error(`Unexpected operation ${operation.type}.`);
@@ -63,8 +95,57 @@ it('activates structured upload data independently of provider presentation', as
     type: 'versions.deploy',
     versions: [{ versionId: next, percentage: 100 }],
   });
+  expect(calls.find((operation) => operation.type === 'versions.deploy')).not.toHaveProperty(
+    'bypassDeploymentChecks',
+  );
 });
 
+it.each([
+  { failure: 'readiness', preserveTriggers: false, reason: 'readiness-failed' },
+  { failure: 'readiness', preserveTriggers: true, reason: 'readiness-failed' },
+  { failure: 'activation', preserveTriggers: false, reason: 'activation-failed' },
+  { failure: 'activation', preserveTriggers: true, reason: 'activation-failed' },
+  { failure: 'triggers', preserveTriggers: false, reason: 'triggers-failed' },
+] as const)(
+  'bypasses deployment checks only for automatic $failure recovery with preserveTriggers=$preserveTriggers',
+  async ({ failure, preserveTriggers, reason }) => {
+    const directory = mkdtempSync(join(tmpdir(), 'void-rollback-checks-'));
+    const configPath = join(directory, 'wrangler.json');
+    writeFileSync(configPath, JSON.stringify({ name: 'site' }));
+    try {
+      const { calls, runWrangler } = setup(
+        { versionId: next },
+        failure === 'readiness' ? undefined : failure,
+      );
+      const result = await activateCloudflareVersion({
+        runWrangler,
+        configPath,
+        workerName: 'site',
+        workersDevSubdomain: 'example',
+        preserveTriggers,
+        verifyUploader: () => true,
+        message: encodeCloudflareVersionMessage([]),
+        readinessAttempts: 1,
+        fetch: async () =>
+          failure === 'readiness'
+            ? new Response('not ready', { status: 503 })
+            : Response.json({ ready: true }),
+      });
+      expect(result).toMatchObject({ ok: false, reason, rollback: 'succeeded' });
+      const deployments = calls.filter((operation) => operation.type === 'versions.deploy');
+      expect(deployments.at(-1)).toMatchObject({
+        versions: [{ versionId: current, percentage: 100 }],
+        bypassDeploymentChecks: true,
+      });
+      for (const operation of deployments.slice(0, -1)) {
+        expect(operation).not.toHaveProperty('bypassDeploymentChecks');
+      }
+    } finally {
+      rmSync(directory, { recursive: true, force: true });
+    }
+  },
+);
+
 it('rejects missing structured upload identity before activation', async () => {
   const { calls, runWrangler } = setup({ unrelated: 'value' });
   const result = await activateCloudflareVersion({
diff --git a/packages/void/src/cli/cf-version-runner.ts b/packages/void/src/cli/cf-version-runner.ts
index c665f2381..a4a94321b 100644
--- a/packages/void/src/cli/cf-version-runner.ts
+++ b/packages/void/src/cli/cf-version-runner.ts
@@ -675,6 +675,7 @@ export function createCfVersionRunner(options: {
                 }),
               ]
             : []),
+          ...(operation.bypassDeploymentChecks ? ['--bypass-deployment-checks'] : []),
         ],
         command.capture,
       );
diff --git a/packages/void/src/cli/cloudflare-operation-process.ts b/packages/void/src/cli/cloudflare-operation-process.ts
index 82c1f4eba..51b77d45a 100644
--- a/packages/void/src/cli/cloudflare-operation-process.ts
+++ b/packages/void/src/cli/cloudflare-operation-process.ts
@@ -1014,6 +1014,7 @@ async function workerHistory(): Promise<Result> {
           versions,
           ...(operation.message ? { annotations: { 'workers/message': operation.message } } : {}),
         }),
+        ...(operation.bypassDeploymentChecks ? ['--bypass-deployment-checks'] : []),
       ]);
     }
     default:
diff --git a/packages/void/src/cli/cloudflare-operations.ts b/packages/void/src/cli/cloudflare-operations.ts
index f2728a4d9..b3102649d 100644
--- a/packages/void/src/cli/cloudflare-operations.ts
+++ b/packages/void/src/cli/cloudflare-operations.ts
@@ -537,6 +537,7 @@ export async function activateCloudflareExistingVersion(
         configPath: context.configPath,
         workerName: context.workerName,
         message: `Void automatic rollback after trigger synchronization failed.`,
+        bypassDeploymentChecks: true,
       },
       { capture: false },
     );
diff --git a/packages/void/src/cli/platform-installer-workers.ts b/packages/void/src/cli/platform-installer-workers.ts
index bdfe30ee8..729953f35 100644
--- a/packages/void/src/cli/platform-installer-workers.ts
+++ b/packages/void/src/cli/platform-installer-workers.ts
@@ -1225,6 +1225,7 @@ export async function restorePlatformWorkerDeployment(input: {
         percentage: version.percentage,
       })),
       message: `Void platform restoration ${input.restoration.id}`,
+      bypassDeploymentChecks: true,
     },
     input.accountId,
     input.directory,
diff --git a/packages/void/test/unit/cf-version-runner.test.ts b/packages/void/test/unit/cf-version-runner.test.ts
index f737eb8a3..45a9cc3af 100644
--- a/packages/void/test/unit/cf-version-runner.test.ts
+++ b/packages/void/test/unit/cf-version-runner.test.ts
@@ -2573,6 +2573,44 @@ it('preserves activation metadata and sorts cf version history for the existing
   }
 });
 
+it.each([undefined, false, true])(
+  'passes bypassDeploymentChecks=%s only when true with and without a deployment body',
+  async (bypassDeploymentChecks) => {
+    const prepared = await output();
+    try {
+      const calls: Array<Array<string>> = [];
+      const runner = createCfVersionRunner({
+        output: prepared,
+        workerName: 'void-test',
+        verifyResources: async () => ({ status: 0, stdout: '', stderr: '' }),
+        runCf: (args) => {
+          calls.push(args);
+          return { status: 0, stdout: '', stderr: '' };
+        },
+      });
+      for (const message of [undefined, 'Void automatic rollback after readiness failed.']) {
+        const result = await runner(
+          {
+            type: 'versions.deploy',
+            workerName: 'void-test',
+            versions: [{ versionId: '00000000-0000-0000-0000-000000000001', percentage: 100 }],
+            message,
+            bypassDeploymentChecks,
+          },
+          { capture: false },
+        );
+        expect(result.status).toBe(0);
+        const args = calls.at(-1)!;
+        expect(args.includes('--bypass-deployment-checks')).toBe(bypassDeploymentChecks === true);
+        expect(args.includes('--body')).toBe(message !== undefined);
+        expect(args).toContain('--versions');
+      }
+    } finally {
+      prepared.dispose();
+    }
+  },
+);
+
 it.each(['newest-first', 'oldest-first'] as const)(
   'reads the actual latest ten versions when cf pages %s',
   async (order) => {
diff --git a/packages/void/test/unit/cloudflare-operation-process.test.ts b/packages/void/test/unit/cloudflare-operation-process.test.ts
index ad948d241..315301253 100644
--- a/packages/void/test/unit/cloudflare-operation-process.test.ts
+++ b/packages/void/test/unit/cloudflare-operation-process.test.ts
@@ -217,6 +217,69 @@ it.each([false, true])(
   },
 );
 
+it.each([undefined, false, true])(
+  'sends bypassDeploymentChecks=%s through cf alongside the deployment body',
+  async (bypassDeploymentChecks) => {
+    const directory = temporaryDirectory('void-cf-deployment-checks-');
+    const requests: Array<{ url: string | undefined; body: unknown }> = [];
+    const api = await listen(
+      createServer(async (request, response) => {
+        let body = '';
+        for await (const chunk of request) {
+          body += chunk;
+        }
+        requests.push({ url: request.url, body: JSON.parse(body) });
+        response.setHeader('Content-Type', 'application/json');
+        response.end(JSON.stringify({ success: true, result: { id: 'deployment-id' } }));
+      }),
+    );
+    const preload = join(directory, 'capture-cf.mjs');
+    const callsPath = join(directory, 'calls.json');
+    writeFileSync(
+      preload,
+      `import child from 'node:child_process';
+import { syncBuiltinESMExports } from 'node:module';
+import { writeFileSync } from 'node:fs';
+const spawnSync = child.spawnSync;
+child.spawnSync = (binary, args, options) => {
+  writeFileSync(${JSON.stringify(callsPath)}, JSON.stringify(args.slice(1)));
+  return spawnSync(binary, args, options);
+};
+syncBuiltinESMExports();
+`,
+    );
+    const versionId = '11111111-1111-4111-8111-111111111111';
+    const message = 'Void automatic rollback after readiness failed.';
+    const output = await runOperation(
+      directory,
+      {
+        type: 'versions.deploy',
+        workerName: 'test-worker',
+        versions: [{ versionId, percentage: 100 }],
+        message,
+        bypassDeploymentChecks,
+      },
+      tokenEnv(api),
+      preload,
+    );
+    expect(output.status, output.stderr).toBe(0);
+    expect(decodeCloudflareOperationResult({ ...output, status: 0 }).status).toBe(0);
+    const args = JSON.parse(readFileSync(callsPath, 'utf8')) as Array<string>;
+    expect(args.includes('--bypass-deployment-checks')).toBe(bypassDeploymentChecks === true);
+    expect(args).toContain('--body');
+    expect(requests).toEqual([
+      {
+        url: `/client/v4/accounts/test-account/workers/scripts/test-worker/deployments${bypassDeploymentChecks === true ? '?force=true' : ''}`,
+        body: {
+          strategy: 'percentage',
+          versions: [{ version_id: versionId, percentage: 100 }],
+          annotations: { 'workers/message': message },
+        },
+      },
+    ]);
+  },
+);
+
 it.each([200, 503])(
   'reports HTTP %i without loading the build toolchain when domain cleanup returns non-JSON',
   async (status) => {
diff --git a/packages/void/test/unit/cloudflare-operations.test.ts b/packages/void/test/unit/cloudflare-operations.test.ts
index e4065e4fe..37308d812 100644
--- a/packages/void/test/unit/cloudflare-operations.test.ts
+++ b/packages/void/test/unit/cloudflare-operations.test.ts
@@ -83,6 +83,7 @@ describe('Cloudflare operational parsing', () => {
       if (args.type === 'versions.deploy') {
         const config = JSON.parse(readFileSync(args.configPath!, 'utf8'));
         expect(config).toEqual({ account_id: 'account-1', name: 'my-worker' });
+        expect(args).not.toHaveProperty('bypassDeploymentChecks');
         active = 'original';
         return ok();
       }
@@ -321,6 +322,7 @@ describe('Cloudflare version operations', () => {
     expect(activation[0].type === 'versions.deploy' ? activation[0].message : undefined).toBe(
       'void:{"schema":2,"migrations":["0000_init.sql"],"triggerConfig":{"workers_dev":true,"preview_urls":true,"routes":[],"crons":["0 * * * *"],"queueConsumers":[],"workflows":[]}}',
     );
+    expect(activation[0]).not.toHaveProperty('bypassDeploymentChecks');
     expect(runner.mock.calls.some(([args]) => args.type === 'triggers.deploy')).toBe(true);
   });
 
@@ -370,12 +372,17 @@ describe('Cloudflare version operations', () => {
       ),
     ).rejects.toThrow(/traffic and triggers were restored to v2/);
     expect(
-      runner.mock.calls.some(
-        ([args]) =>
-          args.type === 'versions.deploy' &&
-          args.versions.some((version) => version.versionId === 'v2' && version.percentage === 100),
-      ),
-    ).toBe(true);
+      runner.mock.calls.filter(([args]) => args.type === 'versions.deploy').map(([args]) => args),
+    ).toEqual([
+      expect.objectContaining({ versions: [{ versionId: 'v1', percentage: 100 }] }),
+      expect.objectContaining({
+        versions: [{ versionId: 'v2', percentage: 100 }],
+        bypassDeploymentChecks: true,
+      }),
+    ]);
+    expect(
+      runner.mock.calls.find(([args]) => args.type === 'versions.deploy')![0],
+    ).not.toHaveProperty('bypassDeploymentChecks');
     expect(runner.mock.calls.filter(([args]) => args.type === 'triggers.deploy')).toHaveLength(2);
     expect(runner.mock.calls.filter(([args]) => args.type === 'triggers.clear-crons')).toHaveLength(
       1,
diff --git a/packages/void/test/unit/platform-installer.test.ts b/packages/void/test/unit/platform-installer.test.ts
index 4bc563a20..839b9d2c2 100644
--- a/packages/void/test/unit/platform-installer.test.ts
+++ b/packages/void/test/unit/platform-installer.test.ts
@@ -1869,6 +1869,7 @@ describe('platform installer', () => {
         { versionId: 'version-b', percentage: 75 },
       ],
       message: 'Void platform restoration deployment-intervening',
+      bypassDeploymentChecks: true,
     });
     expect(commands.some((args) => args.type.endsWith('.delete'))).toBe(false);
   });