diff --git a/x-pack/legacy/plugins/task_manager/task.ts b/x-pack/legacy/plugins/task_manager/task.ts
index dfb8ce6c5f9f95..43e71ed8126328 100644
--- a/x-pack/legacy/plugins/task_manager/task.ts
+++ b/x-pack/legacy/plugins/task_manager/task.ts
@@ -108,10 +108,13 @@ export interface TaskDefinition {
   maxAttempts?: number;
 
   /**
-   * Function that returns the delay in seconds to wait before attempting the
-   * failed task again.
+   * Function that customizes how the task should behave when the task fails. This
+   * function can return `true`, `false` or a Date. True will tell task manager
+   * to retry using default delay logic. False will tell task manager to stop retrying
+   * this task. Date will suggest when to the task manager the task should retry.
+   * This function isn't used for interval type tasks, those retry at the next interval.
    */
-  getRetryDelay?: (attempts: number, error: object) => number;
+  getRetry?: (attempts: number, error: object) => boolean | Date;
 
   /**
    * The numer of workers / slots a running instance of this task occupies.
@@ -145,7 +148,7 @@ export const validateTaskDefinition = Joi.object({
     .min(1)
     .default(1),
   createTaskRunner: Joi.func().required(),
-  getRetryDelay: Joi.func().optional(),
+  getRetry: Joi.func().optional(),
 }).default();
 
 /**
diff --git a/x-pack/legacy/plugins/task_manager/task_runner.test.ts b/x-pack/legacy/plugins/task_manager/task_runner.test.ts
index 95dead2013a269..5ca8e6047bc8d3 100644
--- a/x-pack/legacy/plugins/task_manager/task_runner.test.ts
+++ b/x-pack/legacy/plugins/task_manager/task_runner.test.ts
@@ -6,7 +6,7 @@
 
 import _ from 'lodash';
 import sinon from 'sinon';
-import { minutesFromNow, secondsFromNow } from './lib/intervals';
+import { minutesFromNow } from './lib/intervals';
 import { ConcreteTaskInstance } from './task';
 import { TaskManagerRunner } from './task_runner';
 
@@ -255,20 +255,116 @@ describe('TaskManagerRunner', () => {
     );
   });
 
-  test('uses getRetryDelay function on error when defined', async () => {
-    const initialAttempts = _.random(0, 2);
-    const retryDelay = _.random(15, 100);
+  test('uses getRetry function (returning date) on error when defined', async () => {
+    const initialAttempts = _.random(1, 3);
+    const nextRetry = new Date(Date.now() + _.random(15, 100) * 1000);
+    const id = Date.now().toString();
+    const getRetryStub = sinon.stub().returns(nextRetry);
+    const error = new Error('Dangit!');
+    const { runner, store } = testOpts({
+      instance: {
+        id,
+        attempts: initialAttempts,
+      },
+      definitions: {
+        bar: {
+          getRetry: getRetryStub,
+          createTaskRunner: () => ({
+            async run() {
+              throw error;
+            },
+          }),
+        },
+      },
+    });
+
+    await runner.run();
+
+    sinon.assert.calledOnce(store.update);
+    sinon.assert.calledWith(getRetryStub, initialAttempts, error);
+    const instance = store.update.args[0][0];
+
+    expect(instance.runAt.getTime()).toEqual(nextRetry.getTime());
+  });
+
+  test('uses getRetry function (returning true) on error when defined', async () => {
+    const initialAttempts = _.random(1, 3);
+    const id = Date.now().toString();
+    const getRetryStub = sinon.stub().returns(true);
+    const error = new Error('Dangit!');
+    const { runner, store } = testOpts({
+      instance: {
+        id,
+        attempts: initialAttempts,
+      },
+      definitions: {
+        bar: {
+          getRetry: getRetryStub,
+          createTaskRunner: () => ({
+            async run() {
+              throw error;
+            },
+          }),
+        },
+      },
+    });
+
+    await runner.run();
+
+    sinon.assert.calledOnce(store.update);
+    sinon.assert.calledWith(getRetryStub, initialAttempts, error);
+    const instance = store.update.args[0][0];
+
+    const expectedRunAt = new Date(Date.now() + initialAttempts * 5 * 60 * 1000);
+    expect(instance.runAt.getTime()).toEqual(expectedRunAt.getTime());
+  });
+
+  test('uses getRetry function (returning false) on error when defined', async () => {
+    const initialAttempts = _.random(1, 3);
+    const id = Date.now().toString();
+    const getRetryStub = sinon.stub().returns(false);
+    const error = new Error('Dangit!');
+    const { runner, store } = testOpts({
+      instance: {
+        id,
+        attempts: initialAttempts,
+      },
+      definitions: {
+        bar: {
+          getRetry: getRetryStub,
+          createTaskRunner: () => ({
+            async run() {
+              throw error;
+            },
+          }),
+        },
+      },
+    });
+
+    await runner.run();
+
+    sinon.assert.calledOnce(store.update);
+    sinon.assert.calledWith(getRetryStub, initialAttempts, error);
+    const instance = store.update.args[0][0];
+
+    expect(instance.status).toBe('failed');
+  });
+
+  test('bypasses getRetry function (returning false) on error of a recurring task', async () => {
+    const initialAttempts = _.random(1, 3);
     const id = Date.now().toString();
-    const getRetryDelayStub = sinon.stub().returns(retryDelay);
+    const getRetryStub = sinon.stub().returns(false);
     const error = new Error('Dangit!');
     const { runner, store } = testOpts({
       instance: {
         id,
         attempts: initialAttempts,
+        interval: '1m',
+        startedAt: new Date(),
       },
       definitions: {
         bar: {
-          getRetryDelay: getRetryDelayStub,
+          getRetry: getRetryStub,
           createTaskRunner: () => ({
             async run() {
               throw error;
@@ -281,18 +377,20 @@ describe('TaskManagerRunner', () => {
     await runner.run();
 
     sinon.assert.calledOnce(store.update);
-    sinon.assert.calledWith(getRetryDelayStub, initialAttempts, error);
+    sinon.assert.notCalled(getRetryStub);
     const instance = store.update.args[0][0];
 
-    expect(instance.runAt.getTime()).toEqual(secondsFromNow(retryDelay).getTime());
+    const nextIntervalDelay = 60000; // 1m
+    const expectedRunAt = new Date(Date.now() + nextIntervalDelay);
+    expect(instance.runAt.getTime()).toEqual(expectedRunAt.getTime());
   });
 
-  test('uses getRetryDelay to set retryAt when defined', async () => {
+  test('uses getRetry (returning date) to set retryAt when defined', async () => {
     const id = _.random(1, 20).toString();
-    const initialAttempts = _.random(0, 2);
-    const retryDelay = _.random(15, 100);
+    const initialAttempts = _.random(1, 3);
+    const nextRetry = new Date(Date.now() + _.random(15, 100) * 1000);
     const timeoutMinutes = 1;
-    const getRetryDelayStub = sinon.stub().returns(retryDelay);
+    const getRetryStub = sinon.stub().returns(nextRetry);
     const { runner, store } = testOpts({
       instance: {
         id,
@@ -302,7 +400,7 @@ describe('TaskManagerRunner', () => {
       definitions: {
         bar: {
           timeout: `${timeoutMinutes}m`,
-          getRetryDelay: getRetryDelayStub,
+          getRetry: getRetryStub,
           createTaskRunner: () => ({
             run: async () => undefined,
           }),
@@ -313,14 +411,114 @@ describe('TaskManagerRunner', () => {
     await runner.claimOwnership();
 
     sinon.assert.calledOnce(store.update);
-    sinon.assert.calledWith(getRetryDelayStub, initialAttempts + 1);
+    sinon.assert.calledWith(getRetryStub, initialAttempts + 1);
     const instance = store.update.args[0][0];
 
     expect(instance.retryAt.getTime()).toEqual(
-      secondsFromNow(retryDelay).getTime() + timeoutMinutes * 60 * 1000
+      new Date(nextRetry.getTime() + timeoutMinutes * 60 * 1000).getTime()
     );
   });
 
+  test('uses getRetry (returning true) to set retryAt when defined', async () => {
+    const id = _.random(1, 20).toString();
+    const initialAttempts = _.random(1, 3);
+    const timeoutMinutes = 1;
+    const getRetryStub = sinon.stub().returns(true);
+    const { runner, store } = testOpts({
+      instance: {
+        id,
+        attempts: initialAttempts,
+        interval: undefined,
+      },
+      definitions: {
+        bar: {
+          timeout: `${timeoutMinutes}m`,
+          getRetry: getRetryStub,
+          createTaskRunner: () => ({
+            run: async () => undefined,
+          }),
+        },
+      },
+    });
+
+    await runner.claimOwnership();
+
+    sinon.assert.calledOnce(store.update);
+    sinon.assert.calledWith(getRetryStub, initialAttempts + 1);
+    const instance = store.update.args[0][0];
+
+    const attemptDelay = (initialAttempts + 1) * 5 * 60 * 1000;
+    const timeoutDelay = timeoutMinutes * 60 * 1000;
+    expect(instance.retryAt.getTime()).toEqual(
+      new Date(Date.now() + attemptDelay + timeoutDelay).getTime()
+    );
+  });
+
+  test('uses getRetry (returning false) to set retryAt when defined', async () => {
+    const id = _.random(1, 20).toString();
+    const initialAttempts = _.random(1, 3);
+    const timeoutMinutes = 1;
+    const getRetryStub = sinon.stub().returns(false);
+    const { runner, store } = testOpts({
+      instance: {
+        id,
+        attempts: initialAttempts,
+        interval: undefined,
+      },
+      definitions: {
+        bar: {
+          timeout: `${timeoutMinutes}m`,
+          getRetry: getRetryStub,
+          createTaskRunner: () => ({
+            run: async () => undefined,
+          }),
+        },
+      },
+    });
+
+    await runner.claimOwnership();
+
+    sinon.assert.calledOnce(store.update);
+    sinon.assert.calledWith(getRetryStub, initialAttempts + 1);
+    const instance = store.update.args[0][0];
+
+    expect(instance.retryAt).toBeNull();
+    expect(instance.status).toBe('running');
+  });
+
+  test('bypasses getRetry (returning false) of a recurring task to set retryAt when defined', async () => {
+    const id = _.random(1, 20).toString();
+    const initialAttempts = _.random(1, 3);
+    const timeoutMinutes = 1;
+    const getRetryStub = sinon.stub().returns(false);
+    const { runner, store } = testOpts({
+      instance: {
+        id,
+        attempts: initialAttempts,
+        interval: '1m',
+        startedAt: new Date(),
+      },
+      definitions: {
+        bar: {
+          timeout: `${timeoutMinutes}m`,
+          getRetry: getRetryStub,
+          createTaskRunner: () => ({
+            run: async () => undefined,
+          }),
+        },
+      },
+    });
+
+    await runner.claimOwnership();
+
+    sinon.assert.calledOnce(store.update);
+    sinon.assert.notCalled(getRetryStub);
+    const instance = store.update.args[0][0];
+
+    const timeoutDelay = timeoutMinutes * 60 * 1000;
+    expect(instance.retryAt.getTime()).toEqual(new Date(Date.now() + timeoutDelay).getTime());
+  });
+
   test('Fails non-recurring task when maxAttempts reached', async () => {
     const id = _.random(1, 20).toString();
     const initialAttempts = 3;
@@ -355,11 +553,13 @@ describe('TaskManagerRunner', () => {
   test(`Doesn't fail recurring tasks when maxAttempts reached`, async () => {
     const id = _.random(1, 20).toString();
     const initialAttempts = 3;
+    const intervalSeconds = 10;
     const { runner, store } = testOpts({
       instance: {
         id,
         attempts: initialAttempts,
-        interval: '10s',
+        interval: `${intervalSeconds}s`,
+        startedAt: new Date(),
       },
       definitions: {
         bar: {
@@ -379,7 +579,9 @@ describe('TaskManagerRunner', () => {
     const instance = store.update.args[0][0];
     expect(instance.attempts).toEqual(3);
     expect(instance.status).toEqual('idle');
-    expect(instance.runAt.getTime()).toEqual(minutesFromNow(15).getTime());
+    expect(instance.runAt.getTime()).toEqual(
+      new Date(Date.now() + intervalSeconds * 1000).getTime()
+    );
   });
 
   interface TestOpts {
diff --git a/x-pack/legacy/plugins/task_manager/task_runner.ts b/x-pack/legacy/plugins/task_manager/task_runner.ts
index 49936488739031..082670817bf1dc 100644
--- a/x-pack/legacy/plugins/task_manager/task_runner.ts
+++ b/x-pack/legacy/plugins/task_manager/task_runner.ts
@@ -11,7 +11,6 @@
  */
 
 import Joi from 'joi';
-import Boom from 'boom';
 import { intervalFromDate, intervalFromNow } from './lib/intervals';
 import { Logger } from './lib/logger';
 import { BeforeRunFunction } from './lib/middleware';
@@ -23,6 +22,7 @@ import {
   SanitizedTaskDefinition,
   TaskDictionary,
   validateRunResult,
+  TaskStatus,
 } from './task';
 
 const defaultBackoffPerFailure = 5 * 60 * 1000;
@@ -171,17 +171,21 @@ export class TaskManagerRunner implements TaskRunner {
     const attempts = this.instance.attempts + 1;
     const now = new Date();
 
-    const timeoutDate = intervalFromNow(this.definition.timeout!)!;
-
     try {
       this.instance = await this.store.update({
         ...this.instance,
         status: 'running',
         startedAt: now,
         attempts,
-        retryAt: new Date(
-          timeoutDate.getTime() + this.getRetryDelay(attempts, Boom.clientTimeout())
-        ),
+        retryAt: this.instance.interval
+          ? intervalFromNow(this.definition.timeout)!
+          : this.getRetryDelay({
+              attempts,
+              // Fake an error. This allows retry logic when tasks keep timing out
+              // and lets us set a proper "retryAt" value each time.
+              error: new Error('Task timeout'),
+              addDuration: this.definition.timeout,
+            }),
       });
 
       return true;
@@ -223,7 +227,7 @@ export class TaskManagerRunner implements TaskRunner {
     // recurring task: update the task instance
     const startedAt = this.instance.startedAt!;
     const state = result.state || this.instance.state || {};
-    const status = this.getInstanceStatus();
+    let status: TaskStatus = this.getInstanceStatus();
 
     let runAt;
     if (status === 'failed') {
@@ -233,7 +237,18 @@ export class TaskManagerRunner implements TaskRunner {
       runAt = result.runAt;
     } else if (result.error) {
       // when result.error is truthy, then we're retrying because it failed
-      runAt = new Date(Date.now() + this.getRetryDelay(this.instance.attempts, result.error));
+      const newRunAt = this.instance.interval
+        ? intervalFromDate(startedAt, this.instance.interval)!
+        : this.getRetryDelay({
+            attempts: this.instance.attempts,
+            error: result.error,
+          });
+      if (!newRunAt) {
+        status = 'failed';
+        runAt = this.instance.runAt;
+      } else {
+        runAt = newRunAt;
+      }
     } else {
       runAt = intervalFromDate(startedAt, this.instance.interval)!;
     }
@@ -286,11 +301,34 @@ export class TaskManagerRunner implements TaskRunner {
     return this.instance.attempts < maxAttempts ? 'idle' : 'failed';
   }
 
-  private getRetryDelay(attempts: number, error: any) {
-    if (this.definition.getRetryDelay) {
-      return this.definition.getRetryDelay(attempts, error) * 1000;
+  private getRetryDelay({
+    error,
+    attempts,
+    addDuration,
+  }: {
+    error: any;
+    attempts: number;
+    addDuration?: string;
+  }): Date | null {
+    let result = null;
+
+    // Use custom retry logic, if any, otherwise we'll use the default logic
+    const retry: boolean | Date = this.definition.getRetry
+      ? this.definition.getRetry(attempts, error)
+      : true;
+
+    if (retry instanceof Date) {
+      result = retry;
+    } else if (retry === true) {
+      result = new Date(Date.now() + attempts * defaultBackoffPerFailure);
     }
-    return attempts * defaultBackoffPerFailure;
+
+    // Add a duration to the result
+    if (addDuration && result) {
+      result = intervalFromDate(result, addDuration)!;
+    }
+
+    return result;
   }
 }