[Bug]: Desktop stays cloud-disconnected despite healthy Cloud MCP and fresh reinstall

[inesgavinho-byte]

Summary

OpenWork Desktop 0.18.39 on macOS Apple Silicon remains in an unstable Cloud/organization state even after a full clean reinstall. The UI connection indicator repeatedly alternates between connected/warning states, OpenWork Models does not sync correctly, and the Desktop reports the effective Connect branch as cloud-disconnected even though the OpenWork Cloud MCP is healthy and reachable.

The issue reproduces after:

• OpenWork Nuke
• manual removal of OpenWork/OpenCode local state
• deleting /Applications/OpenWork.app
• rebooting macOS
• installing a fresh 0.18.39 build
• creating a fresh local workspace
• signing in with a different account on the same Mac

This strongly suggests the problem is not stale local state.

Environment

• OpenWork Desktop: 0.18.39
• OpenWork Server: 0.18.39
• OpenCode: bundled with OpenWork
• OS: macOS, Apple Silicon
• Organization: Cloud organization with active AI model access

Observed behavior

1. Desktop Cloud status intermittently flips between connected and warning/yellow.
2. Organization policies active is shown on the affected Desktop.
3. OpenWork Models does not become available/synced as expected.
4. A fresh local workspace starts correctly.
5. The local OpenWork server is healthy.
6. Diagnostic report resolves the Connect branch as cloud-disconnected despite the Cloud MCP being injected and reachable.

Key diagnostic evidence

The built-in agent/context diagnostics report:

overall: warning
firstFailedCheck: null
workspace: OPEN WORK
workspace type: local
engineConfigured: true

Workspace/runtime checks pass:

workspace-runtime: passed
workspace_runtime_configured

Connect steering reports:

expectedBranch: cloud-disconnected
connectStateStatus: available
connectEnabled: true
globalCloudMcpPresent: true
selectedWorkspaceCloudMcpPresent: true

The OpenWork agent and canonical prompt resolve correctly:

effective_openwork_agent_selected: passed
effective_prompt_matches_canonical: passed

Managed MCP registration is healthy:

managedMcpCount: 1
enabledManagedMcpCount: 1
connectedCount: 1
failedCount: 0
needsAuthCount: 0
needsClientRegistrationCount: 0
engineReachableNow: true

The Cloud catalog probe succeeds and returns the expected tools:

cloud_catalog_exact_match: passed
httpStatus: 200
observedToolIds:
- search_capabilities
- execute_capability
requiredToolsPresent: true

The runtime and engine both reach the OpenWork Cloud endpoint:

runtime_and_engine_connected: passed
runtimeProbeStatus: observed
runtimeProbeStage: complete
runtimeProbeCode: catalog_observed
engineRegistrationStatus: connected
engineReachableNow: true

The actual managed Cloud MCP entry is:

name: openwork-cloud
source: config.remote
type: remote
enabled: true
origin: https://api.openworklabs.com
path: /mcp/agent
syncStatus: connected

But the organization connection inventory is empty:

organization_connections_ready: passed
connectionCount: 0
reportedConnectionCount: 0
notReadyCount: 0
memberActionCount: 0
organizationAdminActionCount: 0

And the final Connect summary still says:

stateStatus: available
connectEnabled: true
expectedBranch: cloud-disconnected
globalCloudMcpPresent: true
selectedWorkspaceCloudMcpPresent: true
crossWorkspaceSteeringDrift: false

Why this looks inconsistent

The Desktop has all of the following at the same time:

• active local workspace
• healthy OpenWork Server
• effective OpenWork agent
• healthy managed openwork-cloud MCP registration
• successful HTTPS access to https://api.openworklabs.com/mcp/agent
• successful MCP handshake and tools/list
• exact required Cloud tools present

Yet Connect resolves to cloud-disconnected, organization connections are empty, and the Desktop UI remains unstable.

Expected behavior

If the Cloud MCP is connected and the signed-in organization/session is valid, the Desktop should resolve a connected Cloud branch consistently, organization-scoped state should stabilize, and managed providers/models should sync normally.

Actual behavior

The Cloud transport and MCP are healthy, but the Desktop behaves as though the organization/session is disconnected.

Additional notes

The reinstall was intentionally done without restoring any previous OpenWork/OpenCode files. Fresh debug output confirmed no existing desktop-bootstrap.json and no stale bootstrap override.

A separate known issue (#3560) reports OpenWork Models failing to connect after reinstall/reset, but this report adds stronger built-in diagnostic evidence showing the mismatch between healthy Cloud MCP transport and cloud-disconnected Connect state.

No credentials, tokens, prompts, or authorization headers are included here.

[inesgavinho-byte]

Additional evidence after purchasing OpenWork Web for the affected organization:

• OpenWork Web access was purchased successfully for the organization.
• The Web workspace does not provision/start.
• UI shows Workspace needs attention.
• Workspace status shows:
  • Version: Legacy workspace
  • Latest: Not available
  • Backups on
• The resource summary shows AI Providers 0 MODELS.
• Clicking Retry and waiting does not change the state; it returns to the same Workspace needs attention failure.

This means the issue is not limited to the macOS Desktop client. The paid Cloud-hosted Web workspace for the same organization is also failing to provision, while provider/model entitlement is still not materialized (0 MODELS).

Given the prior diagnostics showing healthy MCP/API reachability from Desktop, this now looks like an organization-side Cloud provisioning / entitlement state problem affecting both Desktop organization state and Web workspace provisioning.

Please let us know if you need an organization/workspace identifier or a support-side reset/repro. No credentials or secrets are included here.