Wire up CertificateReportingService to handle report uploads

chrome/browser/safe_browsing/certificate_reporting_service_browsertest.cc

Index: chrome/browser/safe_browsing/certificate_reporting_service_browsertest.cc
diff --git a/chrome/browser/safe_browsing/certificate_reporting_service_browsertest.cc b/chrome/browser/safe_browsing/certificate_reporting_service_browsertest.cc
new file mode 100644
index 0000000000000000000000000000000000000000..89efeca0311f3df3995ac4ff74dc9bebd0059ffb
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+++ b/chrome/browser/safe_browsing/certificate_reporting_service_browsertest.cc
@@ -0,0 +1,676 @@
+// Copyright 2016 The Chromium Authors. All rights reserved.
+// Use of this source code is governed by a BSD-style license that can be
+// found in the LICENSE file.
+
+#include "chrome/browser/safe_browsing/certificate_reporting_service.h"
+
+#include "base/base_switches.h"
+#include "base/command_line.h"
+#include "base/macros.h"
+#include "base/test/histogram_tester.h"
+#include "base/test/simple_test_clock.h"
+#include "base/test/thread_test_helper.h"
+#include "base/time/clock.h"
+#include "base/time/time.h"
+#include "chrome/browser/profiles/profile.h"
+#include "chrome/browser/safe_browsing/certificate_reporting_service_factory.h"
+#include "chrome/browser/safe_browsing/certificate_reporting_service_test_utils.h"
+#include "chrome/browser/ssl/certificate_reporting_test_utils.h"
+#include "chrome/browser/ui/browser.h"
+#include "chrome/browser/ui/tabs/tab_strip_model.h"
+#include "chrome/common/pref_names.h"
+#include "chrome/test/base/in_process_browser_test.h"
+#include "chrome/test/base/ui_test_utils.h"
+#include "components/certificate_reporting/error_report.h"
+#include "components/prefs/pref_service.h"
+#include "components/variations/variations_switches.h"
+#include "content/public/browser/web_contents.h"
+#include "content/public/test/browser_test_utils.h"
+#include "content/public/test/test_utils.h"
+#include "net/dns/mock_host_resolver.h"
+#include "net/test/embedded_test_server/embedded_test_server.h"
+#include "net/url_request/report_sender.h"
+#include "net/url_request/url_request_context_getter.h"
+#include "net/url_request/url_request_filter.h"
+#include "net/url_request/url_request_test_util.h"
+#include "url/scheme_host_port.h"
+
+using certificate_reporting_test_utils::CertificateReportingServiceTestHelper;
+using certificate_reporting_test_utils::ReportExpectation;
+
+namespace {
+
+const char* kFailedReportHistogram = "SSL.CertificateErrorReportFailure";
+
+void CleanUpOnIOThread() {
+  DCHECK_CURRENTLY_ON(content::BrowserThread::IO);
+  net::URLRequestFilter::GetInstance()->ClearHandlers();
+}
+
+}  // namespace
+
+namespace safe_browsing {
+
+// These tests check the whole mechanism to send and queue invalid certificate
+// reports. Each test triggers reports by visiting broken SSL pages. The reports
+// succeed, fail or hang indefinitely. The test waits for the URL requests
+// corresponding to the reports to to be created via the URL request
+// interceptor. When reports are expected to succeed or fail, test teardown
+// checks that there are no in-flight or pending reports in the
+// CertificateReportingService queue. When a report is to be delayed, a single
+// in-flight report is expected in CertificateReportingService. Since the actual
+// URL requests for reports are sent from the IO thread, the tests wait for the
+// IO thread to finish before checking the expected report counts.
+//
+// Note that these browser tests differ from the unit tests in how they check
+// expected reports: Unit tests create a network delegate and observe the
+// destruction of the URL requests, whereas browser tests wait for the URL
+// requests to be created instead.
+class CertificateReportingServiceBrowserTest : public InProcessBrowserTest {
+ public:
+  CertificateReportingServiceBrowserTest()
+      : https_server_(net::EmbeddedTestServer::TYPE_HTTPS),
+        expect_delayed_report_on_teardown_(false) {}
+
+  void SetUpOnMainThread() override {
+    DCHECK_CURRENTLY_ON(content::BrowserThread::UI);
+    host_resolver()->AddRule("*", "127.0.0.1");
+
+    https_server_.SetSSLConfig(net::EmbeddedTestServer::CERT_MISMATCHED_NAME);
+    https_server_.ServeFilesFromSourceDirectory("chrome/test/data");
+    ASSERT_TRUE(https_server_.Start());
+
+    test_helper_.SetUpInterceptor();
+
+    CertificateReportingServiceFactory::GetInstance()
+        ->SetReportEncryptionParamsForTesting(
+            test_helper_.server_public_key(),
+            test_helper_.server_public_key_version());
+    InProcessBrowserTest::SetUpOnMainThread();
+  }
+
+  void TearDownOnMainThread() override {
+    CheckExpectedReportCounts(expect_delayed_report_on_teardown_);
+    content::BrowserThread::PostTask(content::BrowserThread::IO, FROM_HERE,
+                                     base::Bind(&CleanUpOnIOThread));
+    // Check the histogram as the last thing. This makes sure no in-flight
+    // report is missed.
+    if (num_expected_failed_report_ != 0) {
+      histogram_tester_.ExpectUniqueSample(kFailedReportHistogram,
+                                           -net::ERR_SSL_PROTOCOL_ERROR,
+                                           num_expected_failed_report_);
+    } else {
+      histogram_tester_.ExpectTotalCount(kFailedReportHistogram, 0);
+    }
+  }
+
+  void SetUpCommandLine(base::CommandLine* command_line) override {
+    command_line->AppendSwitchASCII(
+        switches::kForceFieldTrials,
+        "ReportCertificateErrors/ShowAndPossiblySend/");
+    // Setting the sending threshold to 1.0 ensures reporting is enabled.
+    command_line->AppendSwitchASCII(
+        variations::switches::kForceFieldTrialParams,
+        "ReportCertificateErrors.ShowAndPossiblySend:sendingThreshold/1.0");
+  }
+
+  CertificateReportingServiceTestHelper* test_helper() { return &test_helper_; }
+
+ protected:
+  CertificateReportingServiceFactory* factory() {
+    return CertificateReportingServiceFactory::GetInstance();
+  }
+
+  // Sends a report using the provided hostname. Navigates to an interstitial
+  // page on this hostname and away from it to trigger a report.
+  void SendReport(const std::string& hostname) {
+    // Create an HTTPS URL from the hostname. This will resolve to the HTTPS
+    // server and cause an SSL error.
+    const GURL kCertErrorURL(
+        url::SchemeHostPort("https", hostname, https_server_.port()).GetURL());
+
+    // Navigate to the page with SSL error.
+    TabStripModel* tab_strip_model = browser()->tab_strip_model();
+    content::WebContents* contents = tab_strip_model->GetActiveWebContents();
+    ui_test_utils::NavigateToURL(browser(), kCertErrorURL);
+    content::WaitForInterstitialAttach(contents);
+
+    // Navigate away from the interstitial to trigger report upload.
+    ui_test_utils::NavigateToURL(browser(), GURL("about:blank"));
+    content::WaitForInterstitialDetach(contents);
+    WaitForIOThread();
+  }
+
+  void SendPendingReports() { service()->SendPending(); }
+
+  // Checks that there are no outstanding reports.
+  // If |expect_delayed_report_on_teardown| is true, expects a single delayed
+  // report.
+  void CheckNoReports() { CheckExpectedReportCounts(false); }
+
+  // Changes opt-in status and waits for the cert reporting service to reset.
+  // Can only be used after the service is initialized. When changing the
+  // value at the beginning of a test,
+  // certificate_reporting_test_utils::SetCertReportingOptIn should be used
+  // instead since the service is only created upon first SSL error.
+  // Changing the opt-in status synchronously fires
+  // CertificateReportingService::PreferenceObserver::OnPreferenceChanged which
+  // will call CertificateReportingService::SetEnabled() which in turn posts
+  // a task to the IO thread to reset the service. Waiting for the IO thread
+  // ensures that the service is reset before returning from this method.
+  void ChangeOptInAndWait(certificate_reporting_test_utils::OptIn opt_in) {
+    certificate_reporting_test_utils::SetCertReportingOptIn(browser(), opt_in);
+    WaitForIOThread();
+  }
+
+  // Same as ChangeOptInAndWait, but enables/disables SafeBrowsing instead.
+  void ToggleSafeBrowsingAndWaitForServiceReset(bool safebrowsing_enabled) {
+    browser()->profile()->GetPrefs()->SetBoolean(prefs::kSafeBrowsingEnabled,
+                                                 safebrowsing_enabled);
+    WaitForIOThread();
+  }
+
+  void ShutdownServiceAndWait() {
+    service()->Shutdown();
+    WaitForIOThread();
+  }
+
+  // Waits for a number of URL requests to be created for the reports in
+  // |expectation| and checks that the reports in |expectation| matches the
+  // reports observed by URL request interceptor.
+  void WaitForReports(const ReportExpectation& expectation) {
+    test_helper_.interceptor()->WaitForReports(expectation.num_reports());
+    std::set<std::string> expected_hostnames;
+    CheckReports(expectation.successful_reports,
+                 test_helper_.interceptor()->successful_reports());
+    CheckReports(expectation.failed_reports,
+                 test_helper_.interceptor()->failed_reports());
+    CheckReports(expectation.delayed_reports,
+                 test_helper_.interceptor()->delayed_reports());
+    test_helper_.interceptor()->ClearObservedReports();
+  }
+
+  // Resumes the delayed request and waits for the resume task to complete which
+  // in turn means the response starts.
+  void ResumeDelayedRequestAndWait() {
+    base::RunLoop run_loop;
+    test_helper_.ResumeDelayedRequest(run_loop.QuitClosure());
+    run_loop.Run();
+  }
+
+  // Tells the test to expect a delayed report during test teardown. If not set,
+  // the tests expect no in-flight reports during teardown.
+  void SetExpectDelayedReportOnTeardown() {
+    expect_delayed_report_on_teardown_ = true;
+  }
+
+  void SetExpectedHistogramCountOnTeardown(
+      unsigned int num_expected_failed_report) {
+    num_expected_failed_report_ = num_expected_failed_report;
+  }
+
+ private:
+  CertificateReportingService* service() const {
+    return CertificateReportingServiceFactory::GetForBrowserContext(
+        browser()->profile());
+  }
+
+  // Waits for pending tasks on the IO thread to complete.
+  void WaitForIOThread() {
+    scoped_refptr<base::ThreadTestHelper> io_helper(new base::ThreadTestHelper(
+        content::BrowserThread::GetTaskRunnerForThread(
+            content::BrowserThread::IO)
+            .get()));
+    ASSERT_TRUE(io_helper->Run());
+  }
+
+  // Checks that the serialized reports in |received_reports| have the same
+  // hostnames as |expected_hostnames|.
+  void CheckReports(const std::set<std::string>& expected_hostnames,
+                    const std::set<std::string>& received_reports) {
+    std::set<std::string> received_hostnames;
+    for (const std::string& serialized_report : received_reports) {
+      certificate_reporting::ErrorReport report;
+      ASSERT_TRUE(report.InitializeFromString(serialized_report));
+      received_hostnames.insert(report.hostname());
+    }
+    EXPECT_EQ(expected_hostnames, received_hostnames);
+  }
+
+  // Checks that there are no remaining successful and failed reports observed
+  // by the interceptor. If |expect_delayed_report| is true, expects a single
+  // delayed report. Otherwise, expects no delayed reports.
+  void CheckExpectedReportCounts(bool expect_delayed_report) {
+    DCHECK_CURRENTLY_ON(content::BrowserThread::UI);
+    // Wait for the IO thread to ensure that any report-sending tasks previously
+    // posted to the IO thread hav run (and thus been observed by the
+    // interceptor).
+    WaitForIOThread();
+    EXPECT_TRUE(test_helper_.interceptor()->successful_reports().empty());
+    EXPECT_TRUE(test_helper_.interceptor()->failed_reports().empty());
+
+    if (expect_delayed_report)
+      EXPECT_EQ(1u, test_helper_.interceptor()->delayed_reports().size());
+    else
+      EXPECT_TRUE(test_helper_.interceptor()->delayed_reports().empty());
+
+    if (service()->GetReporterForTesting()) {
+      // Reporter can be null if reporting is disabled.
+      size_t num_inflight_reports = expect_delayed_report ? 1u : 0u;
+      EXPECT_EQ(num_inflight_reports,
+                service()
+                    ->GetReporterForTesting()
+                    ->inflight_report_count_for_testing());
+    }
+  }
+
+  net::EmbeddedTestServer https_server_;
+  // If true, the test will expect to see a delayed report during test teardown.
+  bool expect_delayed_report_on_teardown_ = false;
+
+  unsigned int num_expected_failed_report_ = 0;
+
+  CertificateReportingServiceTestHelper test_helper_;
+
+  base::HistogramTester histogram_tester_;
+
+  DISALLOW_COPY_AND_ASSIGN(CertificateReportingServiceBrowserTest);
+};
+
+// Tests that report send attempt should be cancelled when extended
+// reporting is not opted in.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       NotOptedIn_ShouldNotSendReports) {
+  SetExpectedHistogramCountOnTeardown(0);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(),
+      certificate_reporting_test_utils::EXTENDED_REPORTING_DO_NOT_OPT_IN);
+  // Send a report. Test teardown checks for created and in-flight requests. If
+  // a report was incorrectly sent, the test will fail.
+  SendReport("no-report");
+}
+
+// Tests that report send attempts are not cancelled when extended reporting is
+// opted in. Goes to an interstitial page and navigates away to force a report
+// send event.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       OptedIn_ShouldSendSuccessfulReport) {
+  SetExpectedHistogramCountOnTeardown(0);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+
+  // Let reports uploads successfully complete.
+  test_helper()->SetFailureMode(certificate_reporting_test_utils::
+                                    ReportSendingResult::REPORTS_SUCCESSFUL);
+
+  // Reporting is opted in, so the report should succeed.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Successful({"report0"}));
+}
+
+// Tests that report send attempts are not cancelled when extended reporting is
+// opted in. Goes to an interstitial page and navigate away to force a report
+// send event. Repeats this three times and checks expected number of reports.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       OptedIn_ShouldQueueFailedReport) {
+  SetExpectedHistogramCountOnTeardown(2);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_FAIL);
+
+  // Send a failed report.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Failed({"report0"}));
+
+  // Send another failed report.
+  SendReport("report1");
+  WaitForReports(ReportExpectation::Failed({"report1"}));
+
+  // Let all report uploads complete successfully now.
+  test_helper()->SetFailureMode(certificate_reporting_test_utils::
+                                    ReportSendingResult::REPORTS_SUCCESSFUL);
+
+  // Send another report. This time the report should be successfully sent.
+  SendReport("report2");
+  WaitForReports(ReportExpectation::Successful({"report2"}));
+
+  // Send all pending reports. The two previously failed reports should have
+  // been queued, and now be sent successfully.
+  SendPendingReports();
+  WaitForReports(ReportExpectation::Successful({"report0", "report1"}));
+
+  // Try sending pending reports again. Since there is no pending report,
+  // nothing should be sent this time. If any report is sent, test teardown
+  // will catch it.
+  SendPendingReports();
+}
+
+// Opting in then opting out of extended reporting should clear the pending
+// report queue.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       OptedIn_ThenOptedOut) {
+  SetExpectedHistogramCountOnTeardown(1);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_FAIL);
+
+  // Send a failed report.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Failed({"report0"}));
+
+  // Disable reporting. This should clear all pending reports.
+  ChangeOptInAndWait(
+      certificate_reporting_test_utils::EXTENDED_REPORTING_DO_NOT_OPT_IN);
+
+  // Send pending reports. No reports should be observed during test teardown.
+  SendPendingReports();
+}
+
+// Opting out, then in, then out of extended reporting should work as expected.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       OptedOut_ThenOptedIn_ThenOptedOut) {
+  SetExpectedHistogramCountOnTeardown(1);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(),
+      certificate_reporting_test_utils::EXTENDED_REPORTING_DO_NOT_OPT_IN);
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_FAIL);
+
+  // Send attempt should be cancelled since reporting is opted out.
+  SendReport("no-report");
+  CheckNoReports();
+
+  // Enable reporting.
+  ChangeOptInAndWait(
+      certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+
+  // A failed report should be observed.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Failed({"report0"}));
+
+  // Disable reporting. This should reset the reporting service and
+  // clear all pending reports.
+  ChangeOptInAndWait(
+      certificate_reporting_test_utils::EXTENDED_REPORTING_DO_NOT_OPT_IN);
+
+  // Report should be cancelled since reporting is opted out.
+  SendReport("report1");
+  CheckNoReports();
+
+  // Send pending reports. Nothing should be sent since there aren't any
+  // pending reports. If any report is sent, test teardown will catch it.
+  SendPendingReports();
+}
+
+// Disabling SafeBrowsing should clear pending reports queue in
+// CertificateReportingService.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       DisableSafebrowsing) {
+  SetExpectedHistogramCountOnTeardown(2);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_FAIL);
+
+  // Send a failed report.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Failed({"report0"}));
+
+  // Disable SafeBrowsing. This should clear all pending reports.
+  ToggleSafeBrowsingAndWaitForServiceReset(false);
+
+  // Send pending reports. No reports should be observed.
+  SendPendingReports();
+  CheckNoReports();
+
+  // Re-enable SafeBrowsing and trigger another report which will be queued.
+  ToggleSafeBrowsingAndWaitForServiceReset(true);
+  SendReport("report1");
+  WaitForReports(ReportExpectation::Failed({"report1"}));
+
+  // Queued report should now be successfully sent.
+  test_helper()->SetFailureMode(certificate_reporting_test_utils::
+                                    ReportSendingResult::REPORTS_SUCCESSFUL);
+  SendPendingReports();
+  WaitForReports(ReportExpectation::Successful({"report1"}));
+}
+
+// CertificateReportingService should ignore reports older than the report TTL.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       DontSendOldReports) {
+  SetExpectedHistogramCountOnTeardown(5);
+
+  base::SimpleTestClock* clock = new base::SimpleTestClock();
+  base::Time reference_time = base::Time::Now();
+  clock->SetNow(reference_time);
+  factory()->SetClockForTesting(std::unique_ptr<base::Clock>(clock));
+
+  // The service should ignore reports older than 24 hours.
+  factory()->SetQueuedReportTTLForTesting(base::TimeDelta::FromHours(24));
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_FAIL);
+
+  // Send a failed report.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Failed({"report0"}));
+
+  // Advance the clock a bit and trigger another failed report.
+  clock->Advance(base::TimeDelta::FromHours(5));
+  SendReport("report1");
+  WaitForReports(ReportExpectation::Failed({"report1"}));
+
+  // Advance the clock to 20 hours, putting it 25 hours ahead of the reference
+  // time. This makes report0 older than 24 hours. report1 is now 20 hours.
+  clock->Advance(base::TimeDelta::FromHours(20));
+
+  // Send pending reports. report0 should be discarded since it's too old.
+  // report1 should be queued again.
+  SendPendingReports();
+  WaitForReports(ReportExpectation::Failed({"report1"}));
+
+  // Trigger another failed report.
+  SendReport("report2");
+  WaitForReports(ReportExpectation::Failed({"report2"}));
+
+  // Advance the clock 5 hours. report1 will now be 25 hours old.
+  clock->Advance(base::TimeDelta::FromHours(5));
+
+  // Send pending reports. report1 should be discarded since it's too old.
+  // report2 should be queued again.
+  SendPendingReports();
+  WaitForReports(ReportExpectation::Failed({"report2"}));
+
+  // Advance the clock 20 hours again so that report2 is 25 hours old and is
+  // older than max age (24 hours).
+  clock->Advance(base::TimeDelta::FromHours(20));
+
+  // Send pending reports. report2 should be discarded since it's too old. No
+  // other reports remain. If any report is sent, test teardown will catch it.
+  SendPendingReports();
+}
+
+// CertificateReportingService should drop old reports from its pending report
+// queue, if the queue is full.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       DropOldReportsFromQueue) {
+  SetExpectedHistogramCountOnTeardown(7);
+
+  base::SimpleTestClock* clock = new base::SimpleTestClock();
+  base::Time reference_time = base::Time::Now();
+  clock->SetNow(reference_time);
+  factory()->SetClockForTesting(std::unique_ptr<base::Clock>(clock));
+
+  // The service should queue a maximum of 3 reports and ignore reports older
+  // than 24 hours.
+  factory()->SetQueuedReportTTLForTesting(base::TimeDelta::FromHours(24));
+  factory()->SetMaxQueuedReportCountForTesting(3);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_FAIL);
+
+  // Trigger a failed report.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Failed({"report0"}));
+
+  // Trigger three more reports within five hours of each other. After this:
+  // report0 is 0 hours after reference time (15 hours old).
+  // report1 is 5 hours after reference time (10 hours old).
+  // report2 is 10 hours after reference time (5 hours old).
+  // report3 is 15 hours after reference time (0 hours old).
+  clock->Advance(base::TimeDelta::FromHours(5));
+  SendReport("report1");
+
+  clock->Advance(base::TimeDelta::FromHours(5));
+  SendReport("report2");
+
+  clock->Advance(base::TimeDelta::FromHours(5));
+  SendReport("report3");
+
+  WaitForReports(ReportExpectation::Failed({"report1", "report2", "report3"}));
+
+  // Send pending reports. Four reports were generated above, but the service
+  // only queues three reports, so report0 should be dropped since it's the
+  // oldest.
+  SendPendingReports();
+  WaitForReports(ReportExpectation::Failed({"report1", "report2", "report3"}));
+
+  // Let all reports succeed.
+  test_helper()->SetFailureMode(certificate_reporting_test_utils::
+                                    ReportSendingResult::REPORTS_SUCCESSFUL);
+
+  // Advance the clock 15 hours. Current time is now 30 hours after reference
+  // time, and the ages of reports are now as follows:
+  // report1 is 25 hours old.
+  // report2 is 20 hours old.
+  // report3 is 15 hours old.
+  clock->Advance(base::TimeDelta::FromHours(15));
+
+  // Send pending reports. Only reports 2 and 3 should be sent, report 1
+  // should be ignored because it's too old.
+  SendPendingReports();
+  WaitForReports(ReportExpectation::Successful({"report2", "report3"}));
+}
+
+// Resume a delayed report after CertificateReportingService shuts down. Should
+// not crash.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       Delayed_NotResumed_ShouldNotCrash) {
+  SetExpectedHistogramCountOnTeardown(0);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+  // Let reports hang.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_DELAY);
+
+  // Navigate to and away from an interstitial to trigger a report. The report
+  // is triggered but hangs, so no error or success callbacks should be called.
+  SendReport("no-report");
+
+  SetExpectDelayedReportOnTeardown();
+}
+
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       Delayed_Resumed) {
+  SetExpectedHistogramCountOnTeardown(0);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_DELAY);
+
+  // Trigger a report that hangs.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Delayed({"report0"}));
+
+  // Resume the report upload. The report upload should successfully complete.
+  // The interceptor only observes request creations and not response
+  // completions, so there is nothing to observe.
+  ResumeDelayedRequestAndWait();
+}
+
+// Same as above, but the service is shut down before resuming the delayed
+// request. Should not crash.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest,
+                       Delayed_Resumed_ServiceShutdown) {
+  SetExpectedHistogramCountOnTeardown(0);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_DELAY);
+
+  // Trigger a report that hangs.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Delayed({"report0"}));
+
+  // Shutdown the service. Resuming the delayed request shouldn't crash.
+  ShutdownServiceAndWait();
+
+  // Resume the report upload. The report upload should successfully complete.
+  // The interceptor only observes request creations and not response
+  // completions, so there is nothing to observe.
+  ResumeDelayedRequestAndWait();
+}
+
+// Trigger a delayed report, then disable Safebrowsing. Certificate reporting
+// service should clear its in-flight reports list.
+IN_PROC_BROWSER_TEST_F(CertificateReportingServiceBrowserTest, Delayed_Reset) {
+  SetExpectedHistogramCountOnTeardown(0);
+
+  certificate_reporting_test_utils::SetCertReportingOptIn(
+      browser(), certificate_reporting_test_utils::EXTENDED_REPORTING_OPT_IN);
+  // Let all reports fail.
+  test_helper()->SetFailureMode(
+      certificate_reporting_test_utils::ReportSendingResult::REPORTS_DELAY);
+
+  // Trigger a report that hangs.
+  SendReport("report0");
+  WaitForReports(ReportExpectation::Delayed({"report0"}));
+
+  // Disable SafeBrowsing. This should clear all pending reports.
+  ToggleSafeBrowsingAndWaitForServiceReset(false);
+
+  // Resume delayed report. No response should be observed since all pending
+  // reports should be cleared.
+  ResumeDelayedRequestAndWait();
+  CheckNoReports();
+
+  // Re-enable SafeBrowsing.
+  ToggleSafeBrowsingAndWaitForServiceReset(true);
+
+  // Trigger a report that hangs.
+  SendReport("report1");
+  WaitForReports(ReportExpectation::Delayed({"report1"}));
+
+  // Resume delayed report. By the time the runloop is finished, the response
+  // will be complete and CertificateReportingService will process the
+  // error/success callback for the report. There will be no inflight reports
+  // remaining.
+  ResumeDelayedRequestAndWait();
+}
+
+}  // namespace safe_browsing