Make environment setup completion observable to the task and platform

apps/worker/src/commands/resume.ts

@@ -47,6 +47,7 @@ export async function resume(runId: number): Promise<boolean> {
       repoPaths,
       repoLocalSkills,
       workspaceReadinessWarnings,
+      backgroundEnvironmentSetup,
       callbacks: defaultCallbacks,
       context,
       logger,
@@ -96,6 +97,7 @@ export async function resume(runId: number): Promise<boolean> {
         repoPaths,
         repoLocalSkills,
         workspaceReadinessWarnings,
+        backgroundEnvironmentSetup,
         orgAgentInstructions: jobContext.orgAgentInstructions,
         styleGuidance: jobContext.styleGuidance,
         agentInstructions:

apps/worker/src/commands/run.ts

@@ -55,6 +55,7 @@ export async function run({
       repoPaths,
       repoLocalSkills,
       workspaceReadinessWarnings,
+      backgroundEnvironmentSetup,
       cancelSignal,
       callbacks,
       context,
@@ -76,6 +77,7 @@ export async function run({
         repoPaths,
         repoLocalSkills,
         workspaceReadinessWarnings,
+        backgroundEnvironmentSetup,
         cancelSignal,
         orgAgentInstructions: jobContext.orgAgentInstructions,
         styleGuidance: jobContext.styleGuidance,

apps/worker/src/commands/setup.ts

@@ -40,6 +40,7 @@ import {
   installOrganizationEnvironmentSkills,
   executeOrganizationEnvironmentRepositoryCommands,
   setupOrganizationEnvironment,
+  EnvironmentSetupStatusWriter,
 } from './setup/index';
 
 export type SetupMode = 'full' | 'directDispatch';
@@ -395,6 +396,17 @@ async function runSetup({
         return;
       }
 
+      // Publish the command plan to <workspace>/.roomote/setup-status.json
+      // before the agent can start, so the sandbox always has an observable
+      // answer to "has environment setup finished?". Created for every
+      // environment workspace — including Docker-only or command-less
+      // setups — because the sandbox instruction and the settle notification
+      // point the agent at this file and must be able to rely on it existing.
+      const setupStatusWriter = new EnvironmentSetupStatusWriter(
+        initializeRepositoriesResult.workspacePath,
+      );
+      setupStatusWriter.initialize(workspace.environmentConfig.repositories);
+
       if (!backgroundEnvironmentSetup) {
         const warnings =
           (await setupOrganizationEnvironment(logger, {
@@ -403,6 +415,8 @@ async function runSetup({
             userEnvVars: workspaceOptions.userEnvVars,
             preparedWorkspace: initializeRepositoriesResult,
             continueRepositoryCommandFailures: continueEnvironmentSetupFailures,
+            setupStatusWriter,
+            recordPhase,
           })) ?? [];
 
         environmentSetupWarnings.push(...warnings);
@@ -423,14 +437,27 @@ async function runSetup({
           'setupOrganizationEnvironmentCommands (background)',
           async () => {
             try {
-              await backgroundDockerProjectsTask;
+              const dockerProjectWarnings =
+                (await backgroundDockerProjectsTask) ?? [];
+
+              // Reflect Docker project failures in the workspace status file
+              // so it never reports a clean `completed` when part of
+              // environment setup went wrong.
+              if (dockerProjectWarnings.length > 0) {
+                setupStatusWriter?.addWarnings(
+                  dockerProjectWarnings.map((warning) => warning.message),
+                );
+              }
+
               const warnings =
                 await executeOrganizationEnvironmentRepositoryCommands(logger, {
                   environment: workspace,
                   envVars: workspaceOptions.envVars,
                   userEnvVars: workspaceOptions.userEnvVars,
                   preparedWorkspace: initializeRepositoriesResult,
                   continueRepositoryCommandFailures: true,
+                  setupStatusWriter,
+                  recordPhase,
                 });
 
               environmentSetupWarnings.push(...warnings);

apps/worker/src/commands/setup/index.ts

@@ -21,4 +21,5 @@ export {
   installOrganizationEnvironmentSkills,
   executeOrganizationEnvironmentRepositoryCommands,
   setupOrganizationEnvironment,
+  EnvironmentSetupStatusWriter,
 } from './workspace';

apps/worker/src/commands/setup/workspace.ts

@@ -8,6 +8,7 @@ export {
   executeOrganizationEnvironmentRepositoryCommands,
   setupOrganizationEnvironment,
 } from './workspace/environment-commands';
+export { EnvironmentSetupStatusWriter } from './workspace/setup-status';
 export { initializeRepositories } from './workspace/repositories';
 export { initializeDockerProjects } from './workspace/docker-projects';
 export {