diff --git a/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/bundled_prebuilt_rules_package/install_latest_bundled_prebuilt_rules.ts b/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/bundled_prebuilt_rules_package/install_latest_bundled_prebuilt_rules.ts
index 33f79b1bff8d..32dbcfe8724a 100644
--- a/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/bundled_prebuilt_rules_package/install_latest_bundled_prebuilt_rules.ts
+++ b/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/bundled_prebuilt_rules_package/install_latest_bundled_prebuilt_rules.ts
@@ -61,7 +61,8 @@ export default ({ getService }: FtrProviderContext): void => {
         es,
         supertest,
         '99.0.0',
-        retry
+        retry,
+        log
       );
 
       // As opposed to "registry"
diff --git a/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/bundled_prebuilt_rules_package/prerelease_packages.ts b/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/bundled_prebuilt_rules_package/prerelease_packages.ts
index 83faf92bf7c8..74e9255269bf 100644
--- a/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/bundled_prebuilt_rules_package/prerelease_packages.ts
+++ b/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/bundled_prebuilt_rules_package/prerelease_packages.ts
@@ -49,7 +49,8 @@ export default ({ getService }: FtrProviderContext): void => {
       const fleetPackageInstallationResponse = await installPrebuiltRulesPackageViaFleetAPI(
         es,
         supertest,
-        retry
+        retry,
+        log
       );
 
       expect(fleetPackageInstallationResponse.items.length).toBe(1);
diff --git a/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/management/fleet_integration.ts b/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/management/fleet_integration.ts
index a9653d759320..1599bfead346 100644
--- a/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/management/fleet_integration.ts
+++ b/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/management/fleet_integration.ts
@@ -49,6 +49,7 @@ export default ({ getService }: FtrProviderContext): void => {
         supertest,
         overrideExistingPackage: true,
         retryService: retry,
+        log,
       });
 
       // Verify that status is updated after package installation
diff --git a/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/update_prebuilt_rules_package/update_prebuilt_rules_package.ts b/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/update_prebuilt_rules_package/update_prebuilt_rules_package.ts
index 688816569c18..008bb44a8a33 100644
--- a/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/update_prebuilt_rules_package/update_prebuilt_rules_package.ts
+++ b/x-pack/test/security_solution_api_integration/test_suites/detections_response/default_license/prebuilt_rules/update_prebuilt_rules_package/update_prebuilt_rules_package.ts
@@ -107,7 +107,8 @@ export default ({ getService }: FtrProviderContext): void => {
         es,
         supertest,
         previousVersion,
-        retry
+        retry,
+        log
       );
 
       expect(installPreviousPackageResponse._meta.install_source).toBe('registry');
@@ -160,7 +161,8 @@ export default ({ getService }: FtrProviderContext): void => {
         es,
         supertest,
         currentVersion,
-        retry
+        retry,
+        log
       );
       expect(installLatestPackageResponse.items.length).toBeGreaterThanOrEqual(0);
 
diff --git a/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/retry.ts b/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/retry.ts
index dafd16aaa9f5..3007448ed895 100644
--- a/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/retry.ts
+++ b/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/retry.ts
@@ -6,7 +6,7 @@
  */
 
 import { RetryService } from '@kbn/ftr-common-functional-services';
-
+import type { ToolingLog } from '@kbn/tooling-log';
 /**
  * Retry wrapper for async supertests, with a maximum number of retries.
  * You can pass in a function that executes a supertest test, and make assertions
@@ -44,15 +44,19 @@ import { RetryService } from '@kbn/ftr-common-functional-services';
 export const retry = async <T>({
   test,
   retryService,
+  utilityName,
   retries = 2,
   timeout = 30000,
   retryDelay = 200,
+  log,
 }: {
   test: () => Promise<T>;
+  utilityName: string;
   retryService: RetryService;
   retries?: number;
   timeout?: number;
   retryDelay?: number;
+  log: ToolingLog;
 }): Promise<T> => {
   let retryAttempt = 0;
   const response = await retryService.tryForTime(
@@ -61,12 +65,23 @@ export const retry = async <T>({
       if (retryAttempt > retries) {
         // Log error message if we reached the maximum number of retries
         // but don't throw an error, return it to break the retry loop.
-        return new Error('Reached maximum number of retries for test.');
+        const errorMessage = `Reached maximum number of retries for test: ${
+          retryAttempt - 1
+        }/${retries}`;
+        log?.error(errorMessage);
+        return new Error(JSON.stringify(errorMessage));
       }
 
       retryAttempt = retryAttempt + 1;
 
-      return test();
+      // Catch the error thrown by the test and log it, then throw it again
+      // to cause `tryForTime` to retry.
+      try {
+        return await test();
+      } catch (error) {
+        log.error(`Retrying ${utilityName}: ${error}`);
+        throw error;
+      }
     },
     undefined,
     retryDelay
diff --git a/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/rules/prebuilt_rules/install_fleet_package_by_url.ts b/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/rules/prebuilt_rules/install_fleet_package_by_url.ts
index 988d73660d0e..2839795ab197 100644
--- a/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/rules/prebuilt_rules/install_fleet_package_by_url.ts
+++ b/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/rules/prebuilt_rules/install_fleet_package_by_url.ts
@@ -9,6 +9,7 @@ import type SuperTest from 'supertest';
 import { InstallPackageResponse } from '@kbn/fleet-plugin/common/types';
 import { epmRouteService } from '@kbn/fleet-plugin/common';
 import { RetryService } from '@kbn/ftr-common-functional-services';
+import type { ToolingLog } from '@kbn/tooling-log';
 import expect from 'expect';
 import { retry } from '../../retry';
 import { refreshSavedObjectIndices } from '../../refresh_index';
@@ -28,7 +29,8 @@ const ATTEMPT_TIMEOUT = 120000;
 export const installPrebuiltRulesPackageViaFleetAPI = async (
   es: Client,
   supertest: SuperTest.SuperTest<SuperTest.Test>,
-  retryService: RetryService
+  retryService: RetryService,
+  log: ToolingLog
 ): Promise<InstallPackageResponse> => {
   const fleetResponse = await retry<InstallPackageResponse>({
     test: async () => {
@@ -44,9 +46,11 @@ export const installPrebuiltRulesPackageViaFleetAPI = async (
 
       return testResponse.body;
     },
+    utilityName: installPrebuiltRulesPackageViaFleetAPI.name,
     retryService,
     retries: MAX_RETRIES,
     timeout: ATTEMPT_TIMEOUT,
+    log,
   });
 
   await refreshSavedObjectIndices(es);
@@ -67,7 +71,8 @@ export const installPrebuiltRulesPackageByVersion = async (
   es: Client,
   supertest: SuperTest.SuperTest<SuperTest.Test>,
   version: string,
-  retryService: RetryService
+  retryService: RetryService,
+  log: ToolingLog
 ): Promise<InstallPackageResponse> => {
   const fleetResponse = await retry<InstallPackageResponse>({
     test: async () => {
@@ -83,9 +88,11 @@ export const installPrebuiltRulesPackageByVersion = async (
 
       return testResponse.body;
     },
+    utilityName: installPrebuiltRulesPackageByVersion.name,
     retryService,
     retries: MAX_RETRIES,
     timeout: ATTEMPT_TIMEOUT,
+    log,
   });
 
   await refreshSavedObjectIndices(es);
diff --git a/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/rules/prebuilt_rules/install_prebuilt_rules_fleet_package.ts b/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/rules/prebuilt_rules/install_prebuilt_rules_fleet_package.ts
index 592406e8c339..770d966f50a5 100644
--- a/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/rules/prebuilt_rules/install_prebuilt_rules_fleet_package.ts
+++ b/x-pack/test/security_solution_api_integration/test_suites/detections_response/utils/rules/prebuilt_rules/install_prebuilt_rules_fleet_package.ts
@@ -15,6 +15,7 @@ import { InstallPackageResponse } from '@kbn/fleet-plugin/common/types';
 import type SuperTest from 'supertest';
 import { RetryService } from '@kbn/ftr-common-functional-services';
 import expect from 'expect';
+import { ToolingLog } from '@kbn/tooling-log';
 import { retry } from '../../retry';
 import { refreshSavedObjectIndices } from '../../refresh_index';
 
@@ -35,12 +36,14 @@ export const installPrebuiltRulesFleetPackage = async ({
   version,
   overrideExistingPackage,
   retryService,
+  log,
 }: {
   es: Client;
   supertest: SuperTest.SuperTest<SuperTest.Test>;
   version?: string;
   overrideExistingPackage: boolean;
   retryService: RetryService;
+  log: ToolingLog;
 }): Promise<InstallPackageResponse | BulkInstallPackagesResponse> => {
   if (version) {
     // Install a specific version
@@ -59,8 +62,10 @@ export const installPrebuiltRulesFleetPackage = async ({
         return testResponse.body;
       },
       retryService,
+      utilityName: installPrebuiltRulesFleetPackage.name,
       retries: MAX_RETRIES,
       timeout: ATTEMPT_TIMEOUT,
+      log,
     });
 
     await refreshSavedObjectIndices(es);
@@ -91,8 +96,10 @@ export const installPrebuiltRulesFleetPackage = async ({
         return body;
       },
       retryService,
+      utilityName: installPrebuiltRulesFleetPackage.name,
       retries: MAX_RETRIES,
       timeout: ATTEMPT_TIMEOUT,
+      log,
     });
 
     await refreshSavedObjectIndices(es);