Add automatic update prompts for out-of-date Cloudflare agent skills by dario-piotrowicz · Pull Request #14872 · cloudflare/workers-sdk

dario-piotrowicz · 2026-07-27T15:30:45Z

Fixes https://jira.cfdata.org/browse/DEVX-2596

We've somewhat recently implemented some logic in Wrangler to, after running some commands from a specific subset, it checks whether the user has Cloudflare Skills installed and if not it asks users wether they'd want Wrangler to install those skills for them.

This PR takes it a small step further. If the user had Wrangler install the Cloudflare Skills for them, then after running one of those commands, it will now check the local Cloudflare Skills against the ones in the Cloudflare repository. If in the repository there are some changes then it will offer the user to update those for them.

Tests
- Tests included/updated
- Automated tests not possible - manual testing has been completed as follows:
- Additional testing not necessary because:
Public documentation
- Cloudflare docs PR(s):
- Documentation not necessary because: self explanatory UX improvement

A picture of a cute animal (not mandatory, but encouraged)

changeset-bot · 2026-07-27T15:30:52Z

🦋 Changeset detected

Latest commit: 6ce0fc3

The changes in this PR will be included in the next version bump.

This PR includes changesets to release 3 packages

Name	Type
wrangler	Minor
@cloudflare/vite-plugin	Patch
@cloudflare/vitest-pool-workers	Patch

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github-actions · 2026-07-27T15:32:38Z

✅ All changesets look good

ask-bonk · 2026-07-27T15:33:04Z

Review posted successfully to PR #14872.

I reviewed the PR and found one actionable logic bug in runSkillsUpdateFlow: on a partial update failure, installedTreeSha is advanced to the remote SHA, which silently marks the failed agents as up-to-date so they're never re-prompted for that revision — inconsistent with the full-failure path, which does re-prompt. I posted a suggestion to only advance installedTreeSha when all agents succeed.

The config/env-var opt-out plumbing, validation, changeset, and metrics event additions all look correct and consistent with existing patterns.

github run

pkg-pr-new · 2026-07-27T15:34:22Z

@cloudflare/autoconfig

npm i https://pkg.pr.new/@cloudflare/autoconfig@14872

@cloudflare/build-output-utils

npm i https://pkg.pr.new/@cloudflare/build-output-utils@14872

@cloudflare/config

npm i https://pkg.pr.new/@cloudflare/config@14872

create-cloudflare

npm i https://pkg.pr.new/create-cloudflare@14872

@cloudflare/deploy-helpers

npm i https://pkg.pr.new/@cloudflare/deploy-helpers@14872

@cloudflare/kv-asset-handler

npm i https://pkg.pr.new/@cloudflare/kv-asset-handler@14872

miniflare

npm i https://pkg.pr.new/miniflare@14872

@cloudflare/pages-functions

npm i https://pkg.pr.new/@cloudflare/pages-functions@14872

@cloudflare/pages-shared

npm i https://pkg.pr.new/@cloudflare/pages-shared@14872

@cloudflare/unenv-preset

npm i https://pkg.pr.new/@cloudflare/unenv-preset@14872

@cloudflare/vite-plugin

npm i https://pkg.pr.new/@cloudflare/vite-plugin@14872

@cloudflare/vitest-pool-workers

npm i https://pkg.pr.new/@cloudflare/vitest-pool-workers@14872

@cloudflare/workers-auth

npm i https://pkg.pr.new/@cloudflare/workers-auth@14872

@cloudflare/workers-editor-shared

npm i https://pkg.pr.new/@cloudflare/workers-editor-shared@14872

@cloudflare/workers-utils

npm i https://pkg.pr.new/@cloudflare/workers-utils@14872

wrangler

npm i https://pkg.pr.new/wrangler@14872

commit: 6ce0fc3

workers-devprod · 2026-07-27T19:53:26Z

Codeowners approval required for this PR:

@cloudflare/wrangler

Show detailed file reviewers

.changeset/skills-update-prompt.md: [@cloudflare/wrangler]
packages/workers-utils/src/environment-variables/factory.ts: [@cloudflare/wrangler]
packages/workers-utils/src/environment-variables/misc-variables.ts: [@cloudflare/wrangler]
packages/wrangler/src/tests/agents-skills-install.test.ts: [@cloudflare/wrangler]
packages/wrangler/src/tests/register-yargs-command-skills.test.ts: [@cloudflare/wrangler]
packages/wrangler/src/tests/vitest.setup.ts: [@cloudflare/wrangler]
packages/wrangler/src/agents-skills-install.ts: [@cloudflare/wrangler]
packages/wrangler/src/core/register-yargs-command.ts: [@cloudflare/wrangler]
packages/wrangler/src/metrics/send-event.ts: [@cloudflare/wrangler]

workers-devprod

Codeowners reviews satisfied

…gnificance heuristic

…names on API failure

workers-devprod · 2026-08-12T12:23:13Z

Codeowners approval required for this PR:

✅ @cloudflare/wrangler

Show detailed file reviewers

workers-devprod added this to workers-sdk Jul 27, 2026

github-project-automation Bot moved this to Untriaged in workers-sdk Jul 27, 2026

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dario-piotrowicz force-pushed the dario/DEVX-2596/update-skills branch 2 times, most recently from 9f8061e to 05e4b46 Compare July 27, 2026 18:19

dario-piotrowicz marked this pull request as ready for review July 27, 2026 19:53

dario-piotrowicz requested a review from workers-devprod as a code owner July 27, 2026 19:53

workers-devprod requested review from a team and edmundhung and removed request for a team July 27, 2026 19:53

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dario-piotrowicz force-pushed the dario/DEVX-2596/update-skills branch from 05e4b46 to 8f3af41 Compare July 27, 2026 20:49

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dario-piotrowicz force-pushed the dario/DEVX-2596/update-skills branch from b3f4ea4 to 3354b4f Compare July 28, 2026 14:40

workers-devprod approved these changes Aug 6, 2026

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github-project-automation Bot moved this from Untriaged to Approved in workers-sdk Aug 6, 2026

dario-piotrowicz added 14 commits August 12, 2026 13:22

Add automatic update prompts for out-of-date Cloudflare agent skills

1c7a68d

also add noSkillsUpdatePrompts for the new wrangler.config.ts

47fc1b3

remove config setting for skipping updates

59ad7ef

replace "are" with "might be"

60a3ccc

simplify skills update check to monthly cadence, remove size-based si…

d0b42a4

…gnificance heuristic

add safer skills installation process

2cd30d1

make sure that partially failed installs are correctly handled

ff48852

handle cross-device renames in skills backup/restore

ecaa31b

back-fill missing skillsTreeSha in cached GitHub response

94fe024

fall back to cached tree SHA in install flow when live fetch fails

5adffe4

preserve backup directory and warn user when skill restore fails

29f8544

fix windows CI issue

38f0bfb

record union of skill names on partial failure and preserve previous …

bece9e3

…names on API failure

address ai reviewers concerns

a969add

dario-piotrowicz force-pushed the dario/DEVX-2596/update-skills branch from 59c2fcd to a969add Compare August 12, 2026 12:22

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dario-piotrowicz added 3 commits August 12, 2026 22:33

use removeDirSync instead of rmSync

b4df9af

align test expectations with redacted telemetry payloads

177537d

add comment explaining currentSkillNames fallback

d1c7c49

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dario-piotrowicz added 2 commits August 12, 2026 23:08

remove raw error message from update failure telemetry

edd3091

make backup dir cleanup fire-and-forget after successful install

6ce0fc3

dario-piotrowicz merged commit 339509d into main Aug 13, 2026
59 checks passed

dario-piotrowicz deleted the dario/DEVX-2596/update-skills branch August 13, 2026 11:03

github-project-automation Bot moved this from Approved to Done in workers-sdk Aug 13, 2026

workers-devprod mentioned this pull request Aug 13, 2026

Version Packages #15154

Merged

brandhaug mentioned this pull request Aug 14, 2026

chore(deps): bump wrangler from 4.122.0 to 4.123.0 brandhaug/b2b-saas-starter#49

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