diff --git a/src/utils/init/agent-skills.ts b/src/utils/init/agent-skills.ts
index 4c28a1a72af..4b8a218a445 100644
--- a/src/utils/init/agent-skills.ts
+++ b/src/utils/init/agent-skills.ts
@@ -613,10 +613,21 @@ export const syncSkills = async ({
           break
         }
         const priorDir = path.join(directory, record.name)
-        if (!currentPresent && (await isSameEntry(priorDir, path.join(directory, record.currentName)))) {
-          await fs.rename(priorDir, path.join(directory, record.currentName))
-          installed.add(record.currentName)
+        const currentDir = path.join(directory, record.currentName)
+        if (!currentPresent && (await isSameEntry(priorDir, currentDir))) {
+          await fs.rename(priorDir, currentDir)
           act(record.name, 'renamed', `-> ${record.currentName}`)
+          if (
+            (await hashIfPossible(currentDir, skill)) !== skill.tree_hash &&
+            (await install(skill, { force: reset }))
+          ) {
+            if (record.modified) {
+              act(record.currentName, 'reset', `edited copy replaced with ${skill.version ?? 'latest'}`)
+            } else {
+              act(record.currentName, 'updated', `-> ${skill.version ?? 'latest'}`)
+            }
+          }
+          installed.add(record.currentName)
           break
         }
         if (!currentPresent && !(await install(skill))) {
@@ -715,7 +726,12 @@ const describeSync = ({ directory, actions }: SkillsSyncResult): string => {
   if (changed + summary.failed === 0) {
     return `Netlify skills in ${location} are up to date${parts.length > 0 ? ` (${parts.join(', ')})` : ''}.`
   }
-  const verb = changed === summary.added ? 'Installed' : 'Synced'
+  if (changed === 0) {
+    return summary.current + summary.kept > 0
+      ? `Some Netlify skills in ${location} could not be synced (${parts.join(', ')}).`
+      : `Could not sync Netlify skills in ${location} (${parts.join(', ')}).`
+  }
+  const verb = changed === summary.added && summary.failed === 0 ? 'Installed' : 'Synced'
   return `${verb} Netlify skills in ${location} (${parts.join(', ')}).`
 }
 
diff --git a/tests/unit/utils/init/agent-skills.test.ts b/tests/unit/utils/init/agent-skills.test.ts
index 8e9edc42ed2..745912519ea 100644
--- a/tests/unit/utils/init/agent-skills.test.ts
+++ b/tests/unit/utils/init/agent-skills.test.ts
@@ -522,6 +522,64 @@ describe('agent skills', () => {
       expect(second.actions.map(({ action }) => action)).toEqual(['current', 'current'])
     })
 
+    test('refreshes a stale copy in the same run when its old name differs only by case', async () => {
+      const deployV1: Files = { 'SKILL.md': '# deploy v1\n' }
+      const caseOnly = buildManifest([
+        FUNCTIONS,
+        { ...DEPLOY, priorNames: ['Netlify-Deploy'], previous: [{ version: '1.0.0', files: deployV1 }] },
+      ])
+      await writeSkill(skillsDir, 'Netlify-Deploy', deployV1)
+      await writeSkill(skillsDir, FUNCTIONS.name, FUNCTIONS.files)
+
+      const { actions } = await syncSkills({ host: HOST, directory: skillsDir, manifest: caseOnly })
+
+      expect(actions).toContainEqual({ name: 'Netlify-Deploy', action: 'renamed', detail: '-> netlify-deploy' })
+      await expect(listDirectories(skillsDir)).resolves.toEqual(['netlify-deploy', 'netlify-functions'])
+      await expect(readFile(join(skillsDir, 'netlify-deploy', 'SKILL.md'), 'utf8')).resolves.toBe('# deploy\n')
+
+      const second = await syncSkills({ host: HOST, directory: skillsDir, manifest: caseOnly })
+      expect(second.actions.map(({ action }) => action)).toEqual(['current', 'current'])
+    })
+
+    test('keeps the old copy when the refresh after a case-only rename fails, and finishes on the next run', async () => {
+      const deployV1: Files = { 'SKILL.md': '# deploy v1\n' }
+      const caseOnly = buildManifest([
+        FUNCTIONS,
+        { ...DEPLOY, priorNames: ['Netlify-Deploy'], previous: [{ version: '1.0.0', files: deployV1 }] },
+      ])
+      await writeSkill(skillsDir, 'Netlify-Deploy', deployV1)
+      await writeSkill(skillsDir, FUNCTIONS.name, FUNCTIONS.files)
+      const deploySkillMd = responses.get('/skills/netlify-deploy/SKILL.md')
+      responses.delete('/skills/netlify-deploy/SKILL.md')
+
+      const { actions } = await syncSkills({ host: HOST, directory: skillsDir, manifest: caseOnly })
+
+      const deployFailures = actions.filter(({ name, action }) => name === 'netlify-deploy' && action === 'failed')
+      expect(deployFailures).toHaveLength(1)
+      expect(deployFailures[0].detail).toMatch(/SKILL\.md: .*HTTP 404/)
+      const [oldCopy] = (await listDirectories(skillsDir)).filter((name) => name.toLowerCase() === 'netlify-deploy')
+      await expect(readFile(join(skillsDir, oldCopy, 'SKILL.md'), 'utf8')).resolves.toBe('# deploy v1\n')
+      await expect(readdir(skillsDir)).resolves.not.toContainEqual(expect.stringMatching(/^\.netlify-skill-/))
+
+      if (deploySkillMd === undefined) throw new Error('netlify-deploy SKILL.md missing from the hosted fixture')
+      responses.set('/skills/netlify-deploy/SKILL.md', deploySkillMd)
+      await syncSkills({ host: HOST, directory: skillsDir, manifest: caseOnly })
+
+      await expect(listDirectories(skillsDir)).resolves.toEqual(['netlify-deploy', 'netlify-functions'])
+      await expect(readFile(join(skillsDir, 'netlify-deploy', 'SKILL.md'), 'utf8')).resolves.toBe('# deploy\n')
+    })
+
+    test('--reset-context replaces an edited copy in the same run when its old name differs only by case', async () => {
+      const caseOnly = buildManifest([FUNCTIONS, { ...DEPLOY, priorNames: ['Netlify-Deploy'] }])
+      await writeSkill(skillsDir, 'Netlify-Deploy', { 'SKILL.md': '# my deploy notes\n' })
+      await writeSkill(skillsDir, FUNCTIONS.name, FUNCTIONS.files)
+
+      await syncSkills({ host: HOST, directory: skillsDir, manifest: caseOnly, reset: true })
+
+      await expect(listDirectories(skillsDir)).resolves.toEqual(['netlify-deploy', 'netlify-functions'])
+      await expect(readFile(join(skillsDir, 'netlify-deploy', 'SKILL.md'), 'utf8')).resolves.toBe('# deploy\n')
+    })
+
     test('leaves a fresh staging directory alone, since another run may still be writing it', async () => {
       await writeSkill(skillsDir, FUNCTIONS.name, FUNCTIONS.files)
       await writeSkill(skillsDir, DEPLOY.name, DEPLOY.files, DEPLOY.executable)
@@ -899,6 +957,29 @@ describe('agent skills', () => {
       expect(lines[2]).toContain('--reset-context')
     })
 
+    test('setupAgentSkills does not say installed when every download failed', async () => {
+      responses.delete('/skills/netlify-functions/SKILL.md')
+      responses.delete('/skills/netlify-deploy/SKILL.md')
+
+      const result = await setupAgentSkills({ workingDir: projectDir, env: { NETLIFY_SKILLS_HOST: HOST } })
+
+      expect(result.installed).toBe(false)
+      expect(result.summary).toMatchObject({ added: 0, failed: 2 })
+      expect(loggedLines()[0]).toMatch(/Could not sync Netlify skills in .*\(2 failed\)\./)
+    })
+
+    test('setupAgentSkills says some skills could not be synced when the rest are already current', async () => {
+      await writeSkill(skillsDir, DEPLOY.name, DEPLOY.files, DEPLOY.executable)
+      await writeSkill(skillsDir, FUNCTIONS.name, FUNCTIONS_V1)
+      responses.delete('/skills/netlify-functions/SKILL.md')
+
+      const result = await setupAgentSkills({ workingDir: projectDir, env: { NETLIFY_SKILLS_HOST: HOST } })
+
+      expect(result.installed).toBe(true)
+      expect(result.summary).toMatchObject({ current: 1, failed: 1 })
+      expect(loggedLines()[0]).toMatch(/Some Netlify skills in .* could not be synced \(1 failed\)\./)
+    })
+
     test('setupAgentSkills reports a failed skill next to what landed', async () => {
       await writeSkill(skillsDir, 'netlify-legacy', RETIRED_FILES)
       responses.delete('/skills/netlify-functions/SKILL.md')