diff --git a/apps/web/components/vcs-split-button.tsx b/apps/web/components/vcs-split-button.tsx
index ec3dc683d7..8d45b90c61 100644
--- a/apps/web/components/vcs-split-button.tsx
+++ b/apps/web/components/vcs-split-button.tsx
@@ -27,6 +27,7 @@ import { Tooltip, TooltipContent, TooltipTrigger } from "@kandev/ui/tooltip";
 import { useSessionGit } from "@/hooks/domains/session/use-session-git";
 import { useGitWithFeedback } from "@/hooks/use-git-with-feedback";
 import { useVcsDialogs } from "@/components/vcs/vcs-dialogs";
+import { useActiveTaskPR } from "@/hooks/domains/github/use-task-pr";
 
 import type { ReactNode } from "react";
 
@@ -34,8 +35,10 @@ function determinePrimaryAction(
   uncommittedFileCount: number,
   aheadCount: number,
   behindCount: number,
-): "commit" | "pr" | "rebase" {
+  hasOpenPR: boolean,
+): "commit" | "push" | "pr" | "rebase" {
   if (uncommittedFileCount > 0) return "commit";
+  if (aheadCount > 0 && hasOpenPR) return "push";
   if (aheadCount > 0) return "pr";
   if (behindCount > 0) return "rebase";
   return "commit";
@@ -75,6 +78,16 @@ function buildPrConfig(aheadCount: number, openPRDialog: () => void): PrimaryBut
   };
 }
 
+function buildPushConfig(aheadCount: number, handlePush: () => void): PrimaryButtonConfig {
+  return {
+    icon: <IconCloudUpload className="h-4 w-4" />,
+    label: "Push",
+    badge: aheadCount > 0 ? aheadCount : null,
+    tooltip: `Push ${aheadCount} commit${aheadCount !== 1 ? "s" : ""} to remote`,
+    onClick: handlePush,
+  };
+}
+
 function buildRebaseConfig(
   behindCount: number,
   baseBranch: string | undefined,
@@ -90,13 +103,14 @@ function buildRebaseConfig(
 }
 
 type PrimaryConfigArgs = {
-  primaryAction: "commit" | "pr" | "rebase";
+  primaryAction: "commit" | "push" | "pr" | "rebase";
   uncommittedFileCount: number;
   aheadCount: number;
   behindCount: number;
   baseBranch: string | undefined;
   openCommitDialog: () => void;
   openPRDialog: () => void;
+  handlePush: () => void;
   handleRebase: () => void;
 };
 
@@ -108,8 +122,10 @@ function buildPrimaryButtonConfig({
   baseBranch,
   openCommitDialog,
   openPRDialog,
+  handlePush,
   handleRebase,
 }: PrimaryConfigArgs): PrimaryButtonConfig {
+  if (primaryAction === "push") return buildPushConfig(aheadCount, handlePush);
   if (primaryAction === "pr") return buildPrConfig(aheadCount, openPRDialog);
   if (primaryAction === "rebase") return buildRebaseConfig(behindCount, baseBranch, handleRebase);
   return buildCommitConfig(uncommittedFileCount, openCommitDialog);
@@ -205,24 +221,8 @@ type VcsSplitButtonProps = {
   baseBranch?: string;
 };
 
-const VcsSplitButton = memo(function VcsSplitButton({
-  sessionId,
-  baseBranch,
-}: VcsSplitButtonProps) {
+function useGitActions(git: ReturnType<typeof useSessionGit>, baseBranch?: string) {
   const gitWithFeedback = useGitWithFeedback();
-  const git = useSessionGit(sessionId);
-  const { openCommitDialog, openPRDialog } = useVcsDialogs();
-
-  const currentBranch = git.branch;
-  const remoteBranch = git.remoteBranch;
-  const hasMatchingUpstream =
-    remoteBranch && currentBranch && remoteBranch === `origin/${currentBranch}`;
-
-  const uncommittedFileCount = git.allFiles.length;
-  const aheadCount = git.ahead;
-  const behindCount = git.behind;
-  const isDisabled = git.isLoading || !sessionId;
-  const isGitLoading = git.isLoading;
 
   const handlePull = useCallback(() => {
     gitWithFeedback(() => git.pull(), "Pull");
@@ -245,7 +245,35 @@ const VcsSplitButton = memo(function VcsSplitButton({
     gitWithFeedback(() => git.merge(targetBranch), "Merge");
   }, [gitWithFeedback, git, baseBranch]);
 
-  const primaryAction = determinePrimaryAction(uncommittedFileCount, aheadCount, behindCount);
+  return { handlePull, handlePush, handleRebase, handleMerge };
+}
+
+const VcsSplitButton = memo(function VcsSplitButton({
+  sessionId,
+  baseBranch,
+}: VcsSplitButtonProps) {
+  const git = useSessionGit(sessionId);
+  const { openCommitDialog, openPRDialog } = useVcsDialogs();
+  const activePR = useActiveTaskPR();
+  const hasOpenPR = activePR?.state === "open";
+  const { handlePull, handlePush, handleRebase, handleMerge } = useGitActions(git, baseBranch);
+
+  const currentBranch = git.branch;
+  const remoteBranch = git.remoteBranch;
+  const hasMatchingUpstream =
+    remoteBranch && currentBranch && remoteBranch === `origin/${currentBranch}`;
+  const uncommittedFileCount = git.allFiles.length;
+  const aheadCount = git.ahead;
+  const behindCount = git.behind;
+  const isDisabled = git.isLoading || !sessionId;
+  const isGitLoading = git.isLoading;
+
+  const primaryAction = determinePrimaryAction(
+    uncommittedFileCount,
+    aheadCount,
+    behindCount,
+    hasOpenPR,
+  );
   const primaryButtonConfig = buildPrimaryButtonConfig({
     primaryAction,
     uncommittedFileCount,
@@ -254,6 +282,7 @@ const VcsSplitButton = memo(function VcsSplitButton({
     baseBranch,
     openCommitDialog,
     openPRDialog,
+    handlePush: () => handlePush(false),
     handleRebase,
   });
 
@@ -267,6 +296,7 @@ const VcsSplitButton = memo(function VcsSplitButton({
             className="rounded-none border-0 cursor-pointer"
             onClick={primaryButtonConfig.onClick}
             disabled={isDisabled}
+            data-testid={`vcs-primary-${primaryAction}`}
           >
             {primaryButtonConfig.icon}
             {primaryButtonConfig.label}
diff --git a/apps/web/e2e/pages/session-page.ts b/apps/web/e2e/pages/session-page.ts
index 8ec86bf62a..81ea6b93ca 100644
--- a/apps/web/e2e/pages/session-page.ts
+++ b/apps/web/e2e/pages/session-page.ts
@@ -281,6 +281,14 @@ export class SessionPage {
     return this.page.getByTestId("pr-topbar-button");
   }
 
+  /** VCS split button primary action. Pass action to match a specific state. */
+  vcsPrimaryButton(action?: "commit" | "push" | "pr" | "rebase"): Locator {
+    if (action) {
+      return this.page.getByTestId(`vcs-primary-${action}`);
+    }
+    return this.page.locator('[data-testid^="vcs-primary-"]');
+  }
+
   /** PR detail panel (auto-shown when task has an associated PR). */
   prDetailPanel(): Locator {
     return this.page.getByTestId("pr-detail-panel");
diff --git a/apps/web/e2e/tests/pr/vcs-button-context.spec.ts b/apps/web/e2e/tests/pr/vcs-button-context.spec.ts
new file mode 100644
index 0000000000..e281bd3a21
--- /dev/null
+++ b/apps/web/e2e/tests/pr/vcs-button-context.spec.ts
@@ -0,0 +1,297 @@
+import { test, expect } from "../../fixtures/test-base";
+import type { ApiClient } from "../../helpers/api-client";
+import { KanbanPage } from "../../pages/kanban-page";
+import { SessionPage } from "../../pages/session-page";
+import type { Page } from "@playwright/test";
+import fs from "node:fs";
+import path from "node:path";
+import { execSync } from "node:child_process";
+
+// ---------------------------------------------------------------------------
+// Helpers
+// ---------------------------------------------------------------------------
+
+class GitHelper {
+  constructor(
+    private repoDir: string,
+    private env: NodeJS.ProcessEnv,
+  ) {}
+
+  exec(cmd: string): string {
+    const lockPath = path.join(this.repoDir, ".git", "index.lock");
+    for (let attempt = 0; attempt < 3; attempt++) {
+      if (fs.existsSync(lockPath)) fs.unlinkSync(lockPath);
+      try {
+        return execSync(cmd, { cwd: this.repoDir, env: this.env, encoding: "utf8" });
+      } catch (err) {
+        const msg = (err as Error).message ?? "";
+        if (msg.includes("index.lock") && attempt < 2) {
+          execSync("sleep 0.2");
+          continue;
+        }
+        throw err;
+      }
+    }
+    throw new Error(`git exec failed after 3 attempts: ${cmd}`);
+  }
+
+  createFile(name: string, content: string) {
+    fs.writeFileSync(path.join(this.repoDir, name), content);
+  }
+
+  /** Set up a bare remote so the local branch can track ahead/behind. */
+  setupRemote(tmpDir: string): void {
+    const bareDir = path.join(tmpDir, "repos", "e2e-repo-bare.git");
+    execSync(`git clone --bare "${this.repoDir}" "${bareDir}"`, { env: this.env });
+    this.exec(`git remote add origin "${bareDir}"`);
+    this.exec("git fetch origin");
+    this.exec("git branch --set-upstream-to=origin/main main");
+  }
+
+  commitFile(name: string, content: string, message: string): void {
+    this.createFile(name, content);
+    this.exec("git add -A");
+    this.exec(`git commit -m "${message}"`);
+  }
+}
+
+async function createStandardProfile(apiClient: ApiClient, name: string) {
+  const { agents } = await apiClient.listAgents();
+  const agentId = agents[0]?.id;
+  if (!agentId) {
+    throw new Error(`E2E setup failed: no agent available for profile "${name}"`);
+  }
+  return apiClient.createAgentProfile(agentId, name, {
+    model: "mock-fast",
+    auto_approve: true,
+    cli_passthrough: false,
+  });
+}
+
+async function openTaskSession(page: Page, title: string): Promise<SessionPage> {
+  const kanban = new KanbanPage(page);
+  await kanban.goto();
+
+  const card = kanban.taskCardByTitle(title);
+  await expect(card).toBeVisible({ timeout: 15_000 });
+  await card.click();
+  await expect(page).toHaveURL(/\/t\//, { timeout: 15_000 });
+
+  const session = new SessionPage(page);
+  await session.waitForLoad();
+  return session;
+}
+
+// ---------------------------------------------------------------------------
+// Tests
+// ---------------------------------------------------------------------------
+
+test.describe("VCS split button context", () => {
+  test("shows Push when PR exists and commits are ahead", async ({
+    testPage,
+    apiClient,
+    seedData,
+    backend,
+  }) => {
+    test.setTimeout(120_000);
+
+    const profile = await createStandardProfile(apiClient, "VCS Push Profile");
+
+    const task = await apiClient.createTaskWithAgent(
+      seedData.workspaceId,
+      "VCS Push Button Test",
+      profile.id,
+      {
+        description: "/e2e:simple-message",
+        workflow_id: seedData.workflowId,
+        workflow_step_id: seedData.startStepId,
+        repository_ids: [seedData.repositoryId],
+      },
+    );
+
+    const session = await openTaskSession(testPage, "VCS Push Button Test");
+    await expect(session.idleInput()).toBeVisible({ timeout: 30_000 });
+
+    // Set up git with a remote so we can get "ahead" status
+    const repoDir = path.join(backend.tmpDir, "repos", "e2e-repo");
+    const gitEnv = {
+      ...process.env,
+      HOME: backend.tmpDir,
+      GIT_AUTHOR_NAME: "E2E Test",
+      GIT_AUTHOR_EMAIL: "e2e@test.local",
+      GIT_COMMITTER_NAME: "E2E Test",
+      GIT_COMMITTER_EMAIL: "e2e@test.local",
+    };
+    const git = new GitHelper(repoDir, gitEnv);
+    git.setupRemote(backend.tmpDir);
+
+    // Make a local commit → now 1 ahead of origin/main
+    git.commitFile("push-test.txt", "push content", "feat: push test commit");
+
+    // Before associating a PR, the button should show "Create PR"
+    // (ahead > 0, no PR)
+    await expect(session.vcsPrimaryButton("pr")).toBeVisible({ timeout: 30_000 });
+
+    // Now associate an open PR with the task
+    await apiClient.mockGitHubReset();
+    await apiClient.mockGitHubSetUser("test-user");
+    await apiClient.mockGitHubAssociateTaskPR({
+      task_id: task.id,
+      owner: "testorg",
+      repo: "testrepo",
+      pr_number: 50,
+      pr_url: "https://github.com/testorg/testrepo/pull/50",
+      pr_title: "Feature branch",
+      head_branch: "main",
+      base_branch: "develop",
+      author_login: "test-user",
+      additions: 10,
+      deletions: 2,
+    });
+
+    // Wait for the PR topbar button to appear (confirms PR is in store)
+    await expect(session.prTopbarButton()).toBeVisible({ timeout: 30_000 });
+
+    // The VCS button should now show "Push" instead of "Create PR"
+    await expect(session.vcsPrimaryButton("push")).toBeVisible({ timeout: 15_000 });
+    await expect(session.vcsPrimaryButton("push")).toContainText("Push");
+  });
+
+  test("shows Create PR when ahead but no PR exists", async ({
+    testPage,
+    apiClient,
+    seedData,
+    backend,
+  }) => {
+    test.setTimeout(120_000);
+
+    const profile = await createStandardProfile(apiClient, "VCS PR Profile");
+
+    await apiClient.createTaskWithAgent(seedData.workspaceId, "VCS PR Button Test", profile.id, {
+      description: "/e2e:simple-message",
+      workflow_id: seedData.workflowId,
+      workflow_step_id: seedData.startStepId,
+      repository_ids: [seedData.repositoryId],
+    });
+
+    const session = await openTaskSession(testPage, "VCS PR Button Test");
+    await expect(session.idleInput()).toBeVisible({ timeout: 30_000 });
+
+    // Set up git with a remote
+    const repoDir = path.join(backend.tmpDir, "repos", "e2e-repo");
+    const gitEnv = {
+      ...process.env,
+      HOME: backend.tmpDir,
+      GIT_AUTHOR_NAME: "E2E Test",
+      GIT_AUTHOR_EMAIL: "e2e@test.local",
+      GIT_COMMITTER_NAME: "E2E Test",
+      GIT_COMMITTER_EMAIL: "e2e@test.local",
+    };
+    const git = new GitHelper(repoDir, gitEnv);
+
+    // Only set up remote if not already configured
+    try {
+      git.exec("git remote get-url origin");
+    } catch {
+      git.setupRemote(backend.tmpDir);
+    }
+
+    // Push current state to origin, then make a new commit to be ahead
+    git.exec("git push origin main");
+    git.commitFile("pr-test.txt", "pr content", "feat: pr test commit");
+
+    // No PR associated → should show "Create PR"
+    await expect(session.vcsPrimaryButton("pr")).toBeVisible({ timeout: 30_000 });
+    await expect(session.vcsPrimaryButton("pr")).toContainText("Create PR");
+  });
+
+  test("shows Commit when there are uncommitted files even with open PR", async ({
+    testPage,
+    apiClient,
+    seedData,
+    backend,
+  }) => {
+    test.setTimeout(120_000);
+
+    const profile = await createStandardProfile(apiClient, "VCS Commit Profile");
+
+    const task = await apiClient.createTaskWithAgent(
+      seedData.workspaceId,
+      "VCS Commit Priority Test",
+      profile.id,
+      {
+        description: "/e2e:simple-message",
+        workflow_id: seedData.workflowId,
+        workflow_step_id: seedData.startStepId,
+        repository_ids: [seedData.repositoryId],
+      },
+    );
+
+    const session = await openTaskSession(testPage, "VCS Commit Priority Test");
+    await expect(session.idleInput()).toBeVisible({ timeout: 30_000 });
+
+    // Associate an open PR
+    await apiClient.mockGitHubReset();
+    await apiClient.mockGitHubSetUser("test-user");
+    await apiClient.mockGitHubAssociateTaskPR({
+      task_id: task.id,
+      owner: "testorg",
+      repo: "testrepo",
+      pr_number: 55,
+      pr_url: "https://github.com/testorg/testrepo/pull/55",
+      pr_title: "Commit Priority PR",
+      head_branch: "main",
+      base_branch: "develop",
+      author_login: "test-user",
+      additions: 5,
+      deletions: 1,
+    });
+
+    await expect(session.prTopbarButton()).toBeVisible({ timeout: 30_000 });
+
+    // Create an uncommitted file
+    const repoDir = path.join(backend.tmpDir, "repos", "e2e-repo");
+    const git = new GitHelper(repoDir, {
+      ...process.env,
+      HOME: backend.tmpDir,
+      GIT_AUTHOR_NAME: "E2E Test",
+      GIT_AUTHOR_EMAIL: "e2e@test.local",
+      GIT_COMMITTER_NAME: "E2E Test",
+      GIT_COMMITTER_EMAIL: "e2e@test.local",
+    });
+    git.createFile("uncommitted.txt", "uncommitted content");
+
+    // Even with open PR, uncommitted files → "Commit" takes priority
+    await expect(session.vcsPrimaryButton("commit")).toBeVisible({ timeout: 30_000 });
+    await expect(session.vcsPrimaryButton("commit")).toContainText("Commit");
+  });
+
+  test("defaults to Commit when no changes and no PR", async ({
+    testPage,
+    apiClient,
+    seedData,
+  }) => {
+    test.setTimeout(120_000);
+
+    const profile = await createStandardProfile(apiClient, "VCS Default Profile");
+
+    await apiClient.createTaskWithAgent(
+      seedData.workspaceId,
+      "VCS Default Button Test",
+      profile.id,
+      {
+        description: "/e2e:simple-message",
+        workflow_id: seedData.workflowId,
+        workflow_step_id: seedData.startStepId,
+        repository_ids: [seedData.repositoryId],
+      },
+    );
+
+    const session = await openTaskSession(testPage, "VCS Default Button Test");
+    await expect(session.idleInput()).toBeVisible({ timeout: 30_000 });
+
+    // No changes, no PR → default is "Commit"
+    await expect(session.vcsPrimaryButton("commit")).toBeVisible({ timeout: 15_000 });
+    await expect(session.vcsPrimaryButton("commit")).toContainText("Commit");
+  });
+});