diff --git a/src/worker/runner/test-runner/index.js b/src/worker/runner/test-runner/index.js
index 7a022dadf..df9577c29 100644
--- a/src/worker/runner/test-runner/index.js
+++ b/src/worker/runner/test-runner/index.js
@@ -14,6 +14,7 @@ const { filterExtraStackFrames } = require("../../../browser/stacktrace/utils");
 const { extendWithCodeSnippet } = require("../../../error-snippets");
 const { startSelectivity } = require("../../../browser/cdp/selectivity");
 const { noopProfilerRuntime } = require("../../../profiler/runtime/noop");
+const { flushSessionManagerErrors } = require("@testplane/webdriverio");
 
 const SNAPSHOTS_TIMEOUT_MS = 10000;
 const SNAPSHOTS_WARNING_TIMEOUT_MS = 2000;
@@ -108,6 +109,25 @@ module.exports = class TestRunner {
     async finishRun(error) {
         const testplaneCtx = this._test.testplaneCtx;
         const { callstackHistory } = this._browser;
+        let additionalContextError;
+
+        // Older WebdriverIO versions do not expose the test-boundary check.
+        if (typeof flushSessionManagerErrors === "function") {
+            try {
+                await flushSessionManagerErrors(this._browser.publicAPI);
+            } catch (contextError) {
+                // A failed context update may leave the session pointing at a stale frame.
+                // The master pool discards browsers marked as broken instead of reusing them.
+                if (!this._browser.state.isBroken) {
+                    this._browser.markAsBroken({ stubBrowserCommands: true });
+                }
+                if (error && error !== contextError) {
+                    additionalContextError = contextError;
+                } else {
+                    error = contextError;
+                }
+            }
+        }
 
         const assertViewResults = testplaneCtx.assertViewResults;
         if (!error && assertViewResults && assertViewResults.hasFails()) {
@@ -172,6 +192,10 @@ module.exports = class TestRunner {
             // The original cause must be removed to avoid possible duplicates later.
             delete error.cause;
 
+            if (additionalContextError) {
+                error.stack += `\n\nAdditional context manager error: ${additionalContextError.stack}`;
+            }
+
             await extendWithCodeSnippet(error);
 
             throw Object.assign(error, results);
diff --git a/test/src/worker/runner/test-runner/index.js b/test/src/worker/runner/test-runner/index.js
index 42b517a8f..bbfdc938d 100644
--- a/test/src/worker/runner/test-runner/index.js
+++ b/test/src/worker/runner/test-runner/index.js
@@ -19,6 +19,7 @@ describe("worker/runner/test-runner", () => {
     const sandbox = sinon.createSandbox();
     let historyRunGroupStub;
     let captureFailScreenshotStub;
+    let flushSessionManagerErrorsStub;
     let TestRunner;
 
     const mkTest_ = (opts = {}) => {
@@ -91,6 +92,7 @@ describe("worker/runner/test-runner", () => {
     beforeEach(() => {
         historyRunGroupStub = sandbox.stub().callsFake(history.runGroup);
         captureFailScreenshotStub = sandbox.stub().resolves(null);
+        flushSessionManagerErrorsStub = sandbox.stub().resolves();
 
         TestRunner = proxyquire("src/worker/runner/test-runner", {
             "../../../browser/history": {
@@ -102,6 +104,9 @@ describe("worker/runner/test-runner", () => {
             "./capture-fail-screenshot": {
                 captureFailScreenshot: captureFailScreenshotStub,
             },
+            "@testplane/webdriverio": {
+                flushSessionManagerErrors: flushSessionManagerErrorsStub,
+            },
         });
 
         sandbox.stub(BrowserAgent.prototype, "getBrowser").resolves(mkBrowser_());
@@ -838,6 +843,21 @@ describe("worker/runner/test-runner", () => {
                 assert.calledOnceWith(BrowserAgent.prototype.freeBrowser, browser);
             });
 
+            it("should fail on a context manager error after the last command", async () => {
+                const browser = mkBrowser_();
+                BrowserAgent.prototype.getBrowser.resolves(browser);
+                flushSessionManagerErrorsStub.rejects(new Error("late context failure"));
+
+                await assert.isRejected(run_(), "late context failure");
+
+                assert.calledOnceWithExactly(flushSessionManagerErrorsStub, browser.publicAPI);
+                assert.calledOnceWithExactly(BrowserAgent.prototype.freeBrowser, browser);
+                assert.callOrder(flushSessionManagerErrorsStub, BrowserAgent.prototype.freeBrowser);
+                assert.isTrue(browser.state.isLastTestFailed);
+                assert.calledOnceWithExactly(browser.markAsBroken, { stubBrowserCommands: true });
+                assert.isTrue(browser.state.isBroken);
+            });
+
             it("should release browser after all browser data has been used", async () => {
                 ExecutionThread.create.callsFake(({ browser }) => {
                     ExecutionThread.prototype.run.callsFake(() => {
@@ -976,6 +996,19 @@ describe("worker/runner/test-runner", () => {
                 assert.calledOnceWith(BrowserAgent.prototype.freeBrowser, browser);
             });
 
+            it("should retain the original test error when context manager also fails", async () => {
+                const browser = mkBrowser_();
+                BrowserAgent.prototype.getBrowser.resolves(browser);
+                ExecutionThread.prototype.run.rejects(new Error("test failure"));
+                flushSessionManagerErrorsStub.rejects(new Error("context failure"));
+
+                const error = await run_().catch(err => err);
+                assert.include(error.message, "test failure");
+                assert.include(error.stack, "context failure");
+                assert.calledOnce(flushSessionManagerErrorsStub);
+                assert.calledOnceWithExactly(browser.markAsBroken, { stubBrowserCommands: true });
+            });
+
             [SAVE_HISTORY_MODE.ONLY_FAILED, SAVE_HISTORY_MODE.ALL].forEach(saveHistoryMode => {
                 it(`should pass history if "saveHistory" is ${saveHistoryMode}`, async () => {
                     const history = Symbol();