diff --git a/docs/agent-skill-sharing-implementation-checklist.md b/docs/agent-skill-sharing-implementation-checklist.md
index 52fc49d70e5..00c7225feb8 100644
--- a/docs/agent-skill-sharing-implementation-checklist.md
+++ b/docs/agent-skill-sharing-implementation-checklist.md
@@ -723,6 +723,11 @@ record before the multi-distro gate.
 
 ## 11. Implement and validate SSH targets
 
+The 2026-08-11 live Orca inventory contains only the connected `windows 2` environment and no
+non-local worktree or repository. Real SSH validation therefore requires registering an isolated
+SSH macOS, Ubuntu 20.04, or supported Windows target; implementation and contract tests continue
+without treating the missing external topology as a product failure.
+
 - [x] Define a host-side installer command that invokes the same installer core and structured
       result contract.
 - [x] Transfer immutable packages through the existing SSH/SFTP provider into bounded private
@@ -766,7 +771,10 @@ record before the multi-distro gate.
       URLs, upload policies, download grants, and credentials.
 - [x] Redact sensitive network values before logger invocation, not after ingestion.
 - [x] Audit authorization and lifecycle events without instruction or script contents.
-- [ ] Verify diagnostics and support bundles preserve the same exclusions.
+- [x] Verify diagnostics and support bundles preserve the same exclusions. Desktop install spans
+      map requests and results to bounded labels before the tracer boundary; regression coverage
+      proves raw paths, filenames, manifests, ACL values, durable share URLs, upload policies,
+      download grants, credentials, and raw error text never enter the collected bundle.
 
 ### Security review
 
diff --git a/src/main/skills/skill-install-request-service.ts b/src/main/skills/skill-install-request-service.ts
index 82dd749aaf3..dcd617a0923 100644
--- a/src/main/skills/skill-install-request-service.ts
+++ b/src/main/skills/skill-install-request-service.ts
@@ -13,6 +13,7 @@ import { downloadSkillPackageGrant } from './skill-package-download'
 import { detectSkillProvidersInWsl } from './skill-wsl-provider-detection'
 import { createWslSkillInstallFilesystem } from './skill-wsl-install-filesystem'
 import { skillInstallFailureFromError } from './skill-install-operation-error'
+import { startSkillInstallOperation } from './skill-operation-observability'
 
 type StagedSkillPackage = {
   archivePath: string
@@ -68,6 +69,21 @@ export async function executeSkillInstallRequest(
   dependencies: SkillInstallRequestDependencies
 ): Promise<SkillInstallResult> {
   const request = SkillInstallRequestSchema.parse(input)
+  const operation = startSkillInstallOperation(request)
+  try {
+    const result = await executeParsedSkillInstallRequest(request, dependencies)
+    operation.complete(result)
+    return result
+  } catch (error) {
+    operation.fail(error)
+    throw error
+  }
+}
+
+async function executeParsedSkillInstallRequest(
+  request: SkillInstallRequest,
+  dependencies: SkillInstallRequestDependencies
+): Promise<SkillInstallResult> {
   const destination = await resolveSkillInstallDestination(
     request.destination,
     dependencies.authority
diff --git a/src/main/skills/skill-operation-observability.test.ts b/src/main/skills/skill-operation-observability.test.ts
new file mode 100644
index 00000000000..f113832d12d
--- /dev/null
+++ b/src/main/skills/skill-operation-observability.test.ts
@@ -0,0 +1,127 @@
+import { mkdtempSync, rmSync, writeFileSync } from 'node:fs'
+import { tmpdir } from 'node:os'
+import { join } from 'node:path'
+import { afterEach, beforeEach, describe, expect, it } from 'vitest'
+import type { SkillInstallRequest, SkillInstallResult } from '../../shared/skill-install-contract'
+import { collectBundle } from '../observability/bundle'
+import { _resetTracerForTests, setActiveSink, type TracerSink } from '../observability/tracer'
+import { startSkillInstallOperation } from './skill-operation-observability'
+
+type CapturingSink = TracerSink & { records: unknown[] }
+
+const PRIVATE_VALUES = {
+  localPath: '/Users/private/team skills/payroll-skill.tar.gz',
+  canonicalPath: '/Users/private/.agents/skills/payroll',
+  providerPath: '/Users/private/.codex/skills/payroll',
+  connectionId: 'private-production-ssh',
+  skillName: 'payroll-instructions',
+  filename: 'salary-review.md',
+  manifest: 'manifest={private-instructions}',
+  acl: 'acl=private-user-id',
+  shareUrl: 'orca://skill-share/private-share-id',
+  uploadPolicy: 'policy=private-signed-upload',
+  downloadGrant: 'https://storage.googleapis.com/private-bucket/object?X-Goog-Signature=secret',
+  credential: 'authorization=Bearer private-access-token'
+}
+
+function request(): SkillInstallRequest {
+  return {
+    operationId: 'operation-private',
+    package: {
+      packageId: 'package-123',
+      versionId: 'version-456',
+      packageDigest: 'a'.repeat(64),
+      archiveSha256: 'b'.repeat(64),
+      compressedBytes: 1234
+    },
+    ingress: { kind: 'local-file', path: PRIVATE_VALUES.localPath },
+    destination: {
+      scope: 'global',
+      executionTarget: { kind: 'ssh', connectionId: PRIVATE_VALUES.connectionId }
+    }
+  }
+}
+
+function result(): SkillInstallResult {
+  return {
+    operationId: 'operation-private',
+    status: 'installed',
+    name: PRIVATE_VALUES.skillName,
+    packageDigest: 'a'.repeat(64),
+    canonicalPath: PRIVATE_VALUES.canonicalPath,
+    placements: [
+      {
+        provider: 'codex',
+        path: PRIVATE_VALUES.providerPath,
+        topology: 'provider-alias',
+        status: 'installed'
+      }
+    ]
+  }
+}
+
+let sink: CapturingSink
+let directory: string
+
+beforeEach(() => {
+  sink = {
+    records: [],
+    push(record) {
+      this.records.push(record)
+    },
+    flush() {},
+    close() {}
+  }
+  directory = mkdtempSync(join(tmpdir(), 'orca-skill-observability-'))
+  setActiveSink(sink)
+})
+
+afterEach(() => {
+  _resetTracerForTests()
+  rmSync(directory, { recursive: true, force: true })
+})
+
+describe('skill operation observability', () => {
+  it('maps install results to bounded labels without private operation data', () => {
+    const operation = startSkillInstallOperation(request())
+    operation.complete(result())
+
+    const serialized = JSON.stringify(sink.records)
+    expect(serialized).toContain('package-123')
+    expect(serialized).toContain('version-456')
+    expect(serialized).toContain('global-ssh')
+    expect(serialized).toContain('provider-alias')
+    for (const value of Object.values(PRIVATE_VALUES)) {
+      expect(serialized).not.toContain(value)
+    }
+  })
+
+  it('keeps support bundles free of paths, filenames, share URLs, policies, ACLs, and grants', () => {
+    const operation = startSkillInstallOperation({
+      ...request(),
+      ingress: {
+        kind: 'download-grant',
+        url: PRIVATE_VALUES.downloadGrant,
+        expiresAt: '2030-01-01T00:00:00Z'
+      }
+    })
+    operation.fail(new Error(Object.values(PRIVATE_VALUES).join(' ')))
+    const traceFile = join(directory, 'trace.ndjson')
+    writeFileSync(traceFile, `${sink.records.map((record) => JSON.stringify(record)).join('\n')}\n`)
+
+    const bundle = collectBundle({
+      traceFilePath: traceFile,
+      maxFiles: 1,
+      appVersion: 'test',
+      platform: 'darwin',
+      arch: 'arm64',
+      osRelease: 'test',
+      orcaChannel: 'dev'
+    })
+
+    expect(bundle.payload).toContain('skill-install-unknown')
+    for (const value of Object.values(PRIVATE_VALUES)) {
+      expect(bundle.payload).not.toContain(value)
+    }
+  })
+})
diff --git a/src/main/skills/skill-operation-observability.ts b/src/main/skills/skill-operation-observability.ts
new file mode 100644
index 00000000000..b2ad7f58348
--- /dev/null
+++ b/src/main/skills/skill-operation-observability.ts
@@ -0,0 +1,76 @@
+import type {
+  SkillInstallDestination,
+  SkillInstallRequest,
+  SkillInstallResult,
+  SkillPlacementResult
+} from '../../shared/skill-install-contract'
+import { startSpan, type ActiveSpan } from '../observability/tracer'
+import { skillInstallFailureFromError } from './skill-install-operation-error'
+
+const SAFE_LABEL = /^[a-z0-9][a-z0-9._-]{0,63}$/i
+
+export type SkillInstallOperationSpan = {
+  complete(result: SkillInstallResult): void
+  fail(error: unknown): void
+}
+
+function safeLabel(value: string | undefined, fallback: string): string {
+  return value && SAFE_LABEL.test(value) ? value : fallback
+}
+
+function destinationLabel(destination: SkillInstallDestination): string {
+  if (destination.scope === 'workspace') {
+    return 'workspace'
+  }
+  return `global-${destination.executionTarget?.kind ?? 'host'}`
+}
+
+function recordPlacement(span: ActiveSpan, placement: SkillPlacementResult): void {
+  span.addEvent('skill.placement', {
+    provider: safeLabel(placement.provider, 'unknown'),
+    topology: placement.topology,
+    status: placement.status,
+    errorCategory: safeLabel(placement.errorCategory, 'none')
+  })
+}
+
+export function startSkillInstallOperation(
+  request: SkillInstallRequest
+): SkillInstallOperationSpan {
+  const span = startSpan('skill.install', {
+    attributes: {
+      packageId: request.package.packageId,
+      versionId: request.package.versionId,
+      phase: 'install',
+      destination: destinationLabel(request.destination),
+      transport: request.ingress.kind,
+      compressedBytes: request.package.compressedBytes
+    }
+  })
+  return {
+    complete(result) {
+      span.setAttribute('status', result.status)
+      span.setAttribute('placementCount', result.placements.length)
+      for (const placement of result.placements) {
+        recordPlacement(span, placement)
+      }
+      if (result.status === 'cancelled') {
+        span.interrupt(safeLabel(result.errorCategory, 'skill-install-cancelled'))
+      } else if (result.status === 'failed') {
+        span.fail(safeLabel(result.errorCategory, 'skill-install-failed'))
+      } else {
+        span.end()
+      }
+    },
+    fail(error) {
+      const failure = skillInstallFailureFromError(error)
+      const code = safeLabel(failure?.code, 'skill-install-unknown')
+      span.setAttribute('status', failure?.category === 'cancelled' ? 'cancelled' : 'failed')
+      if (failure?.category === 'cancelled') {
+        span.interrupt(code)
+      } else {
+        span.fail(code)
+      }
+    }
+  }
+}