diff --git a/src/server/services/__tests__/github.test.ts b/src/server/services/__tests__/github.test.ts
new file mode 100644
index 00000000..56b0ce4d
--- /dev/null
+++ b/src/server/services/__tests__/github.test.ts
@@ -0,0 +1,310 @@
+/**
+ * Copyright 2025 GoodRx, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+import mockRedisClient from 'server/lib/__mocks__/redisClientMock';
+import Github from '../github';
+import { DeployStatus, PullRequestStatus } from 'shared/constants';
+import { PushEvent } from '@octokit/webhooks-types';
+
+mockRedisClient();
+
+jest.mock('server/lib/logger', () => ({
+  error: jest.fn(),
+  info: jest.fn(),
+  warn: jest.fn(),
+  debug: jest.fn(),
+  child: jest.fn().mockReturnThis(),
+}));
+
+describe('Github Service - handlePushWebhook', () => {
+  let githubService: Github;
+  let mockDb: any;
+  let mockRedis: any;
+  let mockRedlock: any;
+  let mockQueueManager: any;
+
+  const createMockPushEvent = (
+    repoId: number = 12345,
+    repoName: string = 'test/repo',
+    branchName: string = 'main'
+  ): PushEvent =>
+    ({
+      ref: `refs/heads/${branchName}`,
+      before: '0000000000000000000000000000000000000000',
+      after: 'abc123def456',
+      repository: {
+        id: repoId,
+        full_name: repoName,
+      },
+    } as PushEvent);
+
+  const createMockBuild = (buildId: number, buildUuid: string = 'test-uuid-123') => ({
+    id: buildId,
+    uuid: buildUuid,
+    enableFullYaml: false,
+    trackDefaultBranches: true,
+    pullRequest: {
+      status: PullRequestStatus.OPEN,
+      deployOnUpdate: true,
+    },
+  });
+
+  const createMockDeploy = (buildId: number, status: string = DeployStatus.READY, deployableId: number = 1) => ({
+    id: deployableId,
+    buildId,
+    status,
+    active: true,
+    branchName: 'main',
+    githubRepositoryId: 12345,
+    build: createMockBuild(buildId),
+    service: {
+      branchName: 'main',
+    },
+    deployable: {
+      defaultBranchName: 'main',
+    },
+  });
+
+  beforeEach(() => {
+    jest.clearAllMocks();
+
+    mockDb = {
+      models: {
+        PullRequest: {
+          findOne: jest.fn().mockResolvedValue(null),
+        },
+        Deploy: {
+          query: jest.fn(),
+        },
+      },
+      services: {
+        BuildService: {
+          resolveAndDeployBuildQueue: {
+            add: jest.fn().mockResolvedValue(undefined),
+          },
+        },
+      },
+    };
+
+    mockRedis = {};
+    mockRedlock = {};
+
+    mockQueueManager = {
+      registerQueue: jest.fn().mockReturnValue({
+        add: jest.fn(),
+        process: jest.fn(),
+        on: jest.fn(),
+      }),
+    };
+
+    githubService = new Github(mockDb, mockRedis, mockRedlock, mockQueueManager);
+  });
+
+  describe('Failed Deploy Detection', () => {
+    test('should include githubRepositoryId when no deploys have failed', async () => {
+      const buildId = 100;
+      const mockDeploy = createMockDeploy(buildId, DeployStatus.READY);
+
+      const mockAllDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereNot: jest.fn().mockReturnThis(),
+        withGraphFetched: jest.fn().mockResolvedValue([mockDeploy]),
+      };
+
+      const mockFailedDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereIn: jest.fn().mockResolvedValue([]), // No failed deploys
+      };
+
+      let callCount = 0;
+      mockDb.models.Deploy.query.mockImplementation(() => {
+        callCount++;
+        return callCount === 1 ? mockAllDeploysQuery : mockFailedDeploysQuery;
+      });
+
+      const pushEvent = createMockPushEvent();
+      await githubService.handlePushWebhook(pushEvent);
+
+      expect(mockDb.services.BuildService.resolveAndDeployBuildQueue.add).toHaveBeenCalledWith('resolve-deploy', {
+        buildId,
+        githubRepositoryId: 12345,
+      });
+    });
+
+    test('should omit githubRepositoryId when deploys have ERROR status', async () => {
+      const buildId = 100;
+      const mockDeploy = createMockDeploy(buildId, DeployStatus.READY);
+      const mockFailedDeploy = { id: 1, status: DeployStatus.ERROR, buildId };
+
+      const mockAllDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereNot: jest.fn().mockReturnThis(),
+        withGraphFetched: jest.fn().mockResolvedValue([mockDeploy]),
+      };
+
+      const mockFailedDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereIn: jest.fn().mockResolvedValue([mockFailedDeploy]),
+      };
+
+      let callCount = 0;
+      mockDb.models.Deploy.query.mockImplementation(() => {
+        callCount++;
+        return callCount === 1 ? mockAllDeploysQuery : mockFailedDeploysQuery;
+      });
+
+      const pushEvent = createMockPushEvent();
+      await githubService.handlePushWebhook(pushEvent);
+
+      expect(mockDb.services.BuildService.resolveAndDeployBuildQueue.add).toHaveBeenCalledWith('resolve-deploy', {
+        buildId,
+      });
+
+      const addCall = mockDb.services.BuildService.resolveAndDeployBuildQueue.add.mock.calls[0];
+      expect(addCall[1]).not.toHaveProperty('githubRepositoryId');
+    });
+
+    test('should handle multiple failed deploys correctly', async () => {
+      const buildId = 100;
+      const mockDeploy = createMockDeploy(buildId, DeployStatus.READY);
+      const mockFailedDeploys = [
+        { id: 1, status: DeployStatus.ERROR, buildId },
+        { id: 2, status: DeployStatus.BUILD_FAILED, buildId },
+        { id: 3, status: DeployStatus.DEPLOY_FAILED, buildId },
+      ];
+
+      const mockAllDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereNot: jest.fn().mockReturnThis(),
+        withGraphFetched: jest.fn().mockResolvedValue([mockDeploy]),
+      };
+
+      const mockFailedDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereIn: jest.fn().mockResolvedValue(mockFailedDeploys),
+      };
+
+      let callCount = 0;
+      mockDb.models.Deploy.query.mockImplementation(() => {
+        callCount++;
+        return callCount === 1 ? mockAllDeploysQuery : mockFailedDeploysQuery;
+      });
+
+      const pushEvent = createMockPushEvent();
+      await githubService.handlePushWebhook(pushEvent);
+
+      expect(mockDb.services.BuildService.resolveAndDeployBuildQueue.add).toHaveBeenCalledWith('resolve-deploy', {
+        buildId,
+      });
+    });
+
+    test('should handle multiple builds and check each for failures independently', async () => {
+      const buildId1 = 100;
+      const buildId2 = 200;
+      const mockBuild1 = createMockBuild(buildId1, 'uuid-100');
+      const mockBuild2 = createMockBuild(buildId2, 'uuid-200');
+
+      const mockDeploy1 = { ...createMockDeploy(buildId1), build: mockBuild1 };
+      const mockDeploy2 = { ...createMockDeploy(buildId2), build: mockBuild2 };
+
+      const mockAllDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereNot: jest.fn().mockReturnThis(),
+        withGraphFetched: jest.fn().mockResolvedValue([mockDeploy1, mockDeploy2]),
+      };
+
+      let queryCount = 0;
+      mockDb.models.Deploy.query.mockImplementation(() => {
+        queryCount++;
+        if (queryCount === 1) {
+          return mockAllDeploysQuery;
+        } else if (queryCount === 2) {
+          return {
+            where: jest.fn().mockReturnThis(),
+            whereIn: jest.fn().mockResolvedValue([]),
+          };
+        } else {
+          return {
+            where: jest.fn().mockReturnThis(),
+            whereIn: jest.fn().mockResolvedValue([{ id: 1, status: DeployStatus.ERROR, buildId: buildId2 }]),
+          };
+        }
+      });
+
+      const pushEvent = createMockPushEvent();
+      await githubService.handlePushWebhook(pushEvent);
+
+      expect(mockDb.services.BuildService.resolveAndDeployBuildQueue.add).toHaveBeenNthCalledWith(1, 'resolve-deploy', {
+        buildId: buildId1,
+        githubRepositoryId: 12345,
+      });
+
+      expect(mockDb.services.BuildService.resolveAndDeployBuildQueue.add).toHaveBeenNthCalledWith(2, 'resolve-deploy', {
+        buildId: buildId2,
+      });
+    });
+
+    test('should not add to queue when PR is closed', async () => {
+      const buildId = 100;
+      const mockBuild = {
+        ...createMockBuild(buildId),
+        pullRequest: {
+          status: PullRequestStatus.CLOSED,
+          deployOnUpdate: true,
+        },
+      };
+      const mockDeploy = { ...createMockDeploy(buildId), build: mockBuild };
+
+      const mockAllDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereNot: jest.fn().mockReturnThis(),
+        withGraphFetched: jest.fn().mockResolvedValue([mockDeploy]),
+      };
+
+      mockDb.models.Deploy.query.mockReturnValue(mockAllDeploysQuery);
+
+      const pushEvent = createMockPushEvent();
+      await githubService.handlePushWebhook(pushEvent);
+
+      expect(mockDb.services.BuildService.resolveAndDeployBuildQueue.add).not.toHaveBeenCalled();
+    });
+
+    test('should not add to queue when deployOnUpdate is false', async () => {
+      const buildId = 100;
+      const mockBuild = {
+        ...createMockBuild(buildId),
+        pullRequest: {
+          status: PullRequestStatus.OPEN,
+          deployOnUpdate: false,
+        },
+      };
+      const mockDeploy = { ...createMockDeploy(buildId), build: mockBuild };
+
+      const mockAllDeploysQuery = {
+        where: jest.fn().mockReturnThis(),
+        whereNot: jest.fn().mockReturnThis(),
+        withGraphFetched: jest.fn().mockResolvedValue([mockDeploy]),
+      };
+
+      mockDb.models.Deploy.query.mockReturnValue(mockAllDeploysQuery);
+
+      const pushEvent = createMockPushEvent();
+      await githubService.handlePushWebhook(pushEvent);
+
+      expect(mockDb.services.BuildService.resolveAndDeployBuildQueue.add).not.toHaveBeenCalled();
+    });
+  });
+});
diff --git a/src/server/services/github.ts b/src/server/services/github.ts
index 7a8a48a1..50845508 100644
--- a/src/server/services/github.ts
+++ b/src/server/services/github.ts
@@ -19,7 +19,13 @@ import _ from 'lodash';
 import Service from './_service';
 import rootLogger from 'server/lib/logger';
 import { IssueCommentEvent, PullRequestEvent, PushEvent } from '@octokit/webhooks-types';
-import { GithubPullRequestActions, GithubWebhookTypes, PullRequestStatus, FallbackLabels } from 'shared/constants';
+import {
+  GithubPullRequestActions,
+  GithubWebhookTypes,
+  PullRequestStatus,
+  FallbackLabels,
+  DeployStatus,
+} from 'shared/constants';
 import { QUEUE_NAMES } from 'shared/config';
 import { NextApiRequest } from 'next';
 import * as github from 'server/lib/github';
@@ -327,10 +333,26 @@ export default class GithubService extends Service {
         if (!buildId) {
           logger.error(`[BUILD ${build?.uuid}][handlePushWebhook][buidIdError] No build ID found for this build!`);
         }
-        logger.info(`[BUILD ${build?.uuid}] Deploying build for push on repo: ${repoName} branch: ${branchName}`);
+
+        // Check if any deploys for this build have failed previously
+        const failedDeploys = await models.Deploy.query()
+          .where('buildId', buildId)
+          .where('active', true)
+          .whereIn('status', [DeployStatus.ERROR, DeployStatus.BUILD_FAILED, DeployStatus.DEPLOY_FAILED]);
+
+        const hasFailedDeploys = failedDeploys.length > 0;
+
+        logger.info(
+          `[BUILD ${build?.uuid}] ${
+            hasFailedDeploys
+              ? `Detected ${failedDeploys.length} failed deploy(s). Triggering full redeploy`
+              : 'Deploying build'
+          } for push on repo: ${repoName} branch: ${branchName}`
+        );
+
         await this.db.services.BuildService.resolveAndDeployBuildQueue.add('resolve-deploy', {
           buildId,
-          githubRepositoryId,
+          ...(hasFailedDeploys ? {} : { githubRepositoryId }),
         });
       }
     } catch (error) {