diff --git a/apps/server/execution/orchestrator.test.ts b/apps/server/execution/orchestrator.test.ts
index fb52e13..6cf293d 100644
--- a/apps/server/execution/orchestrator.test.ts
+++ b/apps/server/execution/orchestrator.test.ts
@@ -6,7 +6,12 @@
 
 import { describe, it, expect, vi, beforeEach } from 'vitest';
 import { ExecutionOrchestrator } from './orchestrator.js';
+import { ensureProjectClone } from '../git/project-clones.js';
 import type { BranchManager } from '../git/branch-manager.js';
+
+vi.mock('../git/project-clones.js', () => ({
+  ensureProjectClone: vi.fn().mockResolvedValue('/tmp/test-workspace/clones/test'),
+}));
 import type { PhaseRepository } from '../db/repositories/phase-repository.js';
 import type { TaskRepository } from '../db/repositories/task-repository.js';
 import type { InitiativeRepository } from '../db/repositories/initiative-repository.js';
@@ -39,7 +44,7 @@ function createMockEventBus(): EventBus & { handlers: Map<string, Function[]>; e
 function createMocks() {
   const branchManager: BranchManager = {
     ensureBranch: vi.fn(),
-    mergeBranch: vi.fn().mockResolvedValue({ success: true, message: 'merged' }),
+    mergeBranch: vi.fn().mockResolvedValue({ success: true, message: 'merged', previousRef: 'abc000' }),
     diffBranches: vi.fn().mockResolvedValue(''),
     deleteBranch: vi.fn(),
     branchExists: vi.fn().mockResolvedValue(true),
@@ -51,6 +56,7 @@ function createMocks() {
     checkMergeability: vi.fn().mockResolvedValue({ mergeable: true }),
     fetchRemote: vi.fn(),
     fastForwardBranch: vi.fn(),
+    updateRef: vi.fn(),
   };
 
   const phaseRepository = {
@@ -306,4 +312,58 @@ describe('ExecutionOrchestrator', () => {
       expect(mocks.phaseDispatchManager.completePhase).not.toHaveBeenCalled();
     });
   });
+
+  describe('approveInitiative', () => {
+    function setupApproveTest(mocks: ReturnType<typeof createMocks>) {
+      const initiative = { id: 'init-1', branch: 'cw/test', status: 'pending_review' };
+      const project = { id: 'proj-1', name: 'test', url: 'https://example.com', defaultBranch: 'main' };
+      vi.mocked(mocks.initiativeRepository.findById).mockResolvedValue(initiative as any);
+      vi.mocked(mocks.projectRepository.findProjectsByInitiativeId).mockResolvedValue([project] as any);
+      vi.mocked(mocks.branchManager.branchExists).mockResolvedValue(true);
+      vi.mocked(mocks.branchManager.mergeBranch).mockResolvedValue({ success: true, message: 'ok', previousRef: 'abc000' });
+      return { initiative, project };
+    }
+
+    it('should roll back merge when push fails', async () => {
+      setupApproveTest(mocks);
+      vi.mocked(mocks.branchManager.pushBranch).mockRejectedValue(new Error('non-fast-forward'));
+
+      const orchestrator = createOrchestrator(mocks);
+
+      await expect(orchestrator.approveInitiative('init-1', 'merge_and_push')).rejects.toThrow('non-fast-forward');
+
+      // Should have rolled back the merge by restoring the previous ref
+      expect(mocks.branchManager.updateRef).toHaveBeenCalledWith(
+        expect.any(String),
+        'main',
+        'abc000',
+      );
+
+      // Should NOT have marked initiative as completed
+      expect(mocks.initiativeRepository.update).not.toHaveBeenCalled();
+    });
+
+    it('should complete initiative when push succeeds', async () => {
+      setupApproveTest(mocks);
+
+      const orchestrator = createOrchestrator(mocks);
+
+      await orchestrator.approveInitiative('init-1', 'merge_and_push');
+
+      expect(mocks.branchManager.updateRef).not.toHaveBeenCalled();
+      expect(mocks.initiativeRepository.update).toHaveBeenCalledWith('init-1', { status: 'completed' });
+    });
+
+    it('should not attempt rollback for push_branch strategy', async () => {
+      setupApproveTest(mocks);
+      vi.mocked(mocks.branchManager.pushBranch).mockRejectedValue(new Error('auth failed'));
+
+      const orchestrator = createOrchestrator(mocks);
+
+      await expect(orchestrator.approveInitiative('init-1', 'push_branch')).rejects.toThrow('auth failed');
+
+      // No merge happened, so no rollback needed
+      expect(mocks.branchManager.updateRef).not.toHaveBeenCalled();
+    });
+  });
 });
diff --git a/apps/server/execution/orchestrator.ts b/apps/server/execution/orchestrator.ts
index 9dba50c..5b8c521 100644
--- a/apps/server/execution/orchestrator.ts
+++ b/apps/server/execution/orchestrator.ts
@@ -695,7 +695,18 @@ export class ExecutionOrchestrator {
         if (!result.success) {
           throw new Error(`Failed to merge ${initiative.branch} into ${project.defaultBranch} for project ${project.name}: ${result.message}`);
         }
-        await this.branchManager.pushBranch(clonePath, project.defaultBranch);
+        try {
+          await this.branchManager.pushBranch(clonePath, project.defaultBranch);
+        } catch (pushErr) {
+          // Roll back the merge so the diff doesn't disappear from the review tab.
+          // Without rollback, defaultBranch includes the initiative changes and the
+          // three-dot diff (defaultBranch...initiativeBranch) becomes empty.
+          if (result.previousRef) {
+            log.warn({ project: project.name, previousRef: result.previousRef }, 'push failed — rolling back merge');
+            await this.branchManager.updateRef(clonePath, project.defaultBranch, result.previousRef);
+          }
+          throw pushErr;
+        }
         log.info({ initiativeId, project: project.name }, 'initiative branch merged into default and pushed');
       } else {
         await this.branchManager.pushBranch(clonePath, initiative.branch);
diff --git a/apps/server/git/branch-manager.ts b/apps/server/git/branch-manager.ts
index ceb399c..9ba6d85 100644
--- a/apps/server/git/branch-manager.ts
+++ b/apps/server/git/branch-manager.ts
@@ -88,4 +88,10 @@ export interface BranchManager {
    * (i.e. the branches have diverged).
    */
   fastForwardBranch(repoPath: string, branch: string, remote?: string): Promise<void>;
+
+  /**
+   * Force-update a branch ref to point at a specific commit.
+   * Used to roll back a merge when a subsequent push fails.
+   */
+  updateRef(repoPath: string, branch: string, commitHash: string): Promise<void>;
 }
diff --git a/apps/server/git/simple-git-branch-manager.ts b/apps/server/git/simple-git-branch-manager.ts
index e686a6f..b8147d0 100644
--- a/apps/server/git/simple-git-branch-manager.ts
+++ b/apps/server/git/simple-git-branch-manager.ts
@@ -39,6 +39,9 @@ export class SimpleGitBranchManager implements BranchManager {
     const tempBranch = `cw-merge-${Date.now()}`;
 
     try {
+      // Capture the target branch ref before merge so callers can roll back on push failure
+      const previousRef = (await repoGit.raw(['rev-parse', targetBranch])).trim();
+
       // Create worktree with a temp branch starting at targetBranch's commit
       await repoGit.raw(['worktree', 'add', '-b', tempBranch, tmpPath, targetBranch]);
 
@@ -53,7 +56,7 @@ export class SimpleGitBranchManager implements BranchManager {
         await repoGit.raw(['update-ref', `refs/heads/${targetBranch}`, mergeCommit]);
 
         log.info({ repoPath, sourceBranch, targetBranch }, 'merge completed cleanly');
-        return { success: true, message: `Merged ${sourceBranch} into ${targetBranch}` };
+        return { success: true, message: `Merged ${sourceBranch} into ${targetBranch}`, previousRef };
       } catch (mergeErr) {
         // Check for merge conflicts
         const status = await wtGit.status();
@@ -208,4 +211,10 @@ export class SimpleGitBranchManager implements BranchManager {
     await git.raw(['merge', '--ff-only', remoteBranch, branch]);
     log.info({ repoPath, branch, remoteBranch }, 'fast-forwarded branch');
   }
+
+  async updateRef(repoPath: string, branch: string, commitHash: string): Promise<void> {
+    const git = simpleGit(repoPath);
+    await git.raw(['update-ref', `refs/heads/${branch}`, commitHash]);
+    log.info({ repoPath, branch, commitHash: commitHash.slice(0, 7) }, 'branch ref updated');
+  }
 }
diff --git a/apps/server/git/types.ts b/apps/server/git/types.ts
index 8471b75..51a35b7 100644
--- a/apps/server/git/types.ts
+++ b/apps/server/git/types.ts
@@ -56,6 +56,8 @@ export interface MergeResult {
   conflicts?: string[];
   /** Human-readable message describing the result */
   message: string;
+  /** The target branch's commit hash before the merge (for rollback on push failure) */
+  previousRef?: string;
 }
 
 // =============================================================================