diff --git a/website/src/components/Buttons/Skip.tsx b/website/src/components/Buttons/Skip.tsx
index 74ca0926..8440e348 100644
--- a/website/src/components/Buttons/Skip.tsx
+++ b/website/src/components/Buttons/Skip.tsx
@@ -1,9 +1,63 @@
-import { Button, ButtonProps } from "@chakra-ui/react";
+import {
+  Button,
+  ButtonProps,
+  Menu,
+  MenuButton,
+  MenuItem,
+  MenuList,
+  Modal,
+  ModalBody,
+  ModalCloseButton,
+  ModalContent,
+  ModalFooter,
+  ModalHeader,
+  ModalOverlay,
+  Textarea,
+  useDisclosure,
+} from "@chakra-ui/react";
+import { useState } from "react";
+import { FaChevronDown } from "react-icons/fa";
+
+interface SkipButtonProps extends ButtonProps {
+  onSkip: (reason: string) => void;
+}
+
+export const SkipButton = ({ onSkip, ...props }: SkipButtonProps) => {
+  const { isOpen, onOpen: showModal, onClose: closeModal } = useDisclosure();
+  const [value, setValue] = useState("");
+
+  const onSubmit = () => {
+    onSkip(value);
+    setValue("");
+    closeModal();
+  };
 
-export const SkipButton = ({ children, ...props }: ButtonProps) => {
   return (
-    <Button size="lg" variant="outline" {...props}>
-      {children}
-    </Button>
+    <>
+      <Button size="lg" variant="outline" onClick={showModal} {...props}>
+        Skip
+      </Button>
+      <Modal isOpen={isOpen} onClose={closeModal}>
+        <ModalOverlay />
+        <ModalContent>
+          <ModalHeader>Skip</ModalHeader>
+          <ModalCloseButton />
+          <ModalBody>
+            <Textarea
+              value={value}
+              onChange={(e) => setValue(e.target.value)}
+              resize="none"
+              placeholder="Any feedback on this task?"
+            />
+          </ModalBody>
+
+          <ModalFooter>
+            <Button colorScheme="blue" mr={3} onClick={onSubmit}>
+              Send
+            </Button>
+          </ModalFooter>
+        </ModalContent>
+      </Modal>
+    </>
   );
 };
diff --git a/website/src/components/Survey/TaskControls.tsx b/website/src/components/Survey/TaskControls.tsx
index 4a6d477a..7f419fcb 100644
--- a/website/src/components/Survey/TaskControls.tsx
+++ b/website/src/components/Survey/TaskControls.tsx
@@ -11,7 +11,8 @@ export interface TaskControlsProps {
   tasks: any[];
   className?: string;
   onSubmitResponse: (task: { id: string }) => void;
-  onSkip: () => void;
+  onSkipTask: (task: { id: string }, reason: string) => void;
+  onNextTask: () => void;
 }
 
 export const TaskControls = (props: TaskControlsProps) => {
@@ -31,13 +32,17 @@ export const TaskControls = (props: TaskControlsProps) => {
     >
       <TaskInfo id={props.tasks[0].id} output="Submit your answer" />
       <Flex justify="center" ml="auto" gap={2}>
-        <SkipButton>Skip</SkipButton>
+        <SkipButton
+          onSkip={(reason: string) => {
+            props.onSkipTask(props.tasks[0], reason);
+          }}
+        />
         {endTask.task.type !== "task_done" ? (
           <SubmitButton colorScheme="blue" data-cy="submit" onClick={() => props.onSubmitResponse(props.tasks[0])}>
             Submit
           </SubmitButton>
         ) : (
-          <SubmitButton colorScheme="green" data-cy="next-task" onClick={props.onSkip}>
+          <SubmitButton colorScheme="green" data-cy="next-task" onClick={props.onNextTask}>
             Next Task
           </SubmitButton>
         )}
diff --git a/website/src/components/Tasks/CreateTask.tsx b/website/src/components/Tasks/CreateTask.tsx
index 057177d2..7dcb0d0f 100644
--- a/website/src/components/Tasks/CreateTask.tsx
+++ b/website/src/components/Tasks/CreateTask.tsx
@@ -1,10 +1,22 @@
 import { useState } from "react";
+
 import { Messages } from "src/components/Messages";
 import { TaskControls } from "src/components/Survey/TaskControls";
 import { TrackedTextarea } from "src/components/Survey/TrackedTextarea";
 import { TwoColumnsWithCards } from "src/components/Survey/TwoColumnsWithCards";
+import { TaskType } from "./TaskTypes";
 
-export const CreateTask = ({ tasks, taskType, trigger, mutate, mainBgClasses }) => {
+export interface CreateTaskProps {
+  // we need a task type
+  // eslint-disable-next-line  @typescript-eslint/no-explicit-any
+  tasks: any[];
+  taskType: TaskType;
+  trigger: (update: { id: string; update_type: string; content: { text: string } }) => void;
+  onSkipTask: (task: { id: string }, reason: string) => void;
+  onNextTask: () => void;
+  mainBgClasses: string;
+}
+export const CreateTask = ({ tasks, taskType, trigger, onSkipTask, onNextTask, mainBgClasses }: CreateTaskProps) => {
   const task = tasks[0].task;
 
   const [inputText, setInputText] = useState("");
@@ -20,11 +32,6 @@ export const CreateTask = ({ tasks, taskType, trigger, mutate, mainBgClasses })
     });
   };
 
-  const fetchNextTask = () => {
-    setInputText("");
-    mutate();
-  };
-
   const textChangeHandler = (event: React.ChangeEvent<HTMLTextAreaElement>) => {
     setInputText(event.target.value);
   };
@@ -48,7 +55,15 @@ export const CreateTask = ({ tasks, taskType, trigger, mutate, mainBgClasses })
         </>
       </TwoColumnsWithCards>
 
-      <TaskControls tasks={tasks} onSubmitResponse={submitResponse} onSkip={fetchNextTask} />
+      <TaskControls
+        tasks={tasks}
+        onSubmitResponse={submitResponse}
+        onSkipTask={(task, reason) => {
+          setInputText("");
+          onSkipTask(task, reason);
+        }}
+        onNextTask={onNextTask}
+      />
     </div>
   );
 };
diff --git a/website/src/components/Tasks/EvaluateTask.tsx b/website/src/components/Tasks/EvaluateTask.tsx
index c45d3dbe..3871b2d9 100644
--- a/website/src/components/Tasks/EvaluateTask.tsx
+++ b/website/src/components/Tasks/EvaluateTask.tsx
@@ -5,7 +5,17 @@ import { TaskControlsOverridable } from "src/components/Survey/TaskControlsOverr
 
 import { MessageTable } from "../Messages/MessageTable";
 
-export const EvaluateTask = ({ tasks, trigger, mutate, mainBgClasses }) => {
+export interface EvaluateTaskProps {
+  // we need a task type
+  // eslint-disable-next-line  @typescript-eslint/no-explicit-any
+  tasks: any[];
+  trigger: (update: { id: string; update_type: string; content: { ranking: number[] } }) => void;
+  onSkipTask: (task: { id: string }, reason: string) => void;
+  onNextTask: () => void;
+  mainBgClasses: string;
+}
+
+export const EvaluateTask = ({ tasks, trigger, onSkipTask, onNextTask, mainBgClasses }: EvaluateTaskProps) => {
   const [ranking, setRanking] = useState<number[]>([]);
   const submitResponse = (task) => {
     trigger({
@@ -17,10 +27,6 @@ export const EvaluateTask = ({ tasks, trigger, mutate, mainBgClasses }) => {
     });
   };
 
-  const fetchNextTask = () => {
-    setRanking([]);
-    mutate();
-  };
   let messages = null;
   if (tasks[0].task.conversation) {
     messages = tasks[0].task.conversation.messages;
@@ -45,7 +51,11 @@ export const EvaluateTask = ({ tasks, trigger, mutate, mainBgClasses }) => {
         isValid={ranking.length == tasks[0].task[sortables].length}
         prepareForSubmit={() => setRanking(tasks[0].task[sortables].map((_, idx) => idx))}
         onSubmitResponse={submitResponse}
-        onSkip={fetchNextTask}
+        onSkipTask={(task, reason) => {
+          setRanking([]);
+          onSkipTask(task, reason);
+        }}
+        onNextTask={onNextTask}
       />
     </div>
   );
diff --git a/website/src/components/Tasks/Task.tsx b/website/src/components/Tasks/Task.tsx
index ce9505e9..153e0a93 100644
--- a/website/src/components/Tasks/Task.tsx
+++ b/website/src/components/Tasks/Task.tsx
@@ -1,10 +1,25 @@
 import { CreateTask } from "./CreateTask";
 import { EvaluateTask } from "./EvaluateTask";
 import { TaskCategory, TaskTypes } from "./TaskTypes";
+import useSWRMutation from "swr/mutation";
+import poster from "src/lib/poster";
 
 export const Task = ({ tasks, trigger, mutate, mainBgClasses }) => {
   const task = tasks[0].task;
 
+  const { trigger: sendRejection } = useSWRMutation("/api/reject_task", poster, {
+    onSuccess: async () => {
+      mutate();
+    },
+  });
+
+  const rejectTask = (task: { id: string }, reason: string) => {
+    sendRejection({
+      id: task.id,
+      reason,
+    });
+  };
+
   function taskTypeComponent(type) {
     const taskType = TaskTypes.find((taskType) => taskType.type === type);
     const category = taskType.category;
@@ -14,13 +29,22 @@ export const Task = ({ tasks, trigger, mutate, mainBgClasses }) => {
           <CreateTask
             tasks={tasks}
             trigger={trigger}
-            mutate={mutate}
+            onSkipTask={rejectTask}
+            onNextTask={mutate}
             taskType={taskType}
             mainBgClasses={mainBgClasses}
           />
         );
       case TaskCategory.Evaluate:
-        return <EvaluateTask tasks={tasks} trigger={trigger} mutate={mutate} mainBgClasses={mainBgClasses} />;
+        return (
+          <EvaluateTask
+            tasks={tasks}
+            trigger={trigger}
+            onSkipTask={rejectTask}
+            onNextTask={mutate}
+            mainBgClasses={mainBgClasses}
+          />
+        );
     }
   }
 
diff --git a/website/src/components/Tasks/TaskTypes.tsx b/website/src/components/Tasks/TaskTypes.tsx
index 82ba1917..409e7038 100644
--- a/website/src/components/Tasks/TaskTypes.tsx
+++ b/website/src/components/Tasks/TaskTypes.tsx
@@ -4,7 +4,17 @@ export enum TaskCategory {
   Label = "Label",
 }
 
-export const TaskTypes = [
+export interface TaskType {
+  label: string;
+  desc: string;
+  category: TaskCategory;
+  pathname: string;
+  type: string;
+  overview?: string;
+  instruction?: string;
+}
+
+export const TaskTypes: TaskType[] = [
   // create
   {
     label: "Create Initial Prompts",
diff --git a/website/src/lib/oasst_api_client.ts b/website/src/lib/oasst_api_client.ts
index 86854c21..889d8b5b 100644
--- a/website/src/lib/oasst_api_client.ts
+++ b/website/src/lib/oasst_api_client.ts
@@ -68,6 +68,12 @@ export class OasstApiClient {
     });
   }
 
+  async nackTask(taskId: string, reason: string): Promise<void> {
+    return this.post(`/api/v1/tasks/${taskId}/nack`, {
+      reason,
+    });
+  }
+
   // TODO return a strongly typed Task?
   // This method is used to record interaction with task while fetching next task.
   // This is a raw Json type, so we can't use it to strongly type the task.
diff --git a/website/src/pages/api/new_task/[task_type].ts b/website/src/pages/api/new_task/[task_type].ts
index addcf3d8..9f3be55c 100644
--- a/website/src/pages/api/new_task/[task_type].ts
+++ b/website/src/pages/api/new_task/[task_type].ts
@@ -36,9 +36,6 @@ const handler = async (req, res) => {
     },
   });
 
-  // Update the backend with our Task ID
-  await oasstApiClient.ackTask(task.id, registeredTask.id);
-
   // Send the results to the client.
   res.status(200).json(registeredTask);
 };
diff --git a/website/src/pages/api/reject_task.ts b/website/src/pages/api/reject_task.ts
new file mode 100644
index 00000000..d146c44b
--- /dev/null
+++ b/website/src/pages/api/reject_task.ts
@@ -0,0 +1,29 @@
+import { Prisma } from "@prisma/client";
+import { getToken } from "next-auth/jwt";
+import { oasstApiClient } from "src/lib/oasst_api_client";
+
+const handler = async (req, res) => {
+  const token = await getToken({ req });
+
+  // Return nothing if the user isn't registered.
+  if (!token) {
+    res.status(401).end();
+    return;
+  }
+
+  // Parse out the local task ID and the interaction contents.
+  const { id: frontendId, reason } = await JSON.parse(req.body);
+
+  const registeredTask = await prisma.registeredTask.findUniqueOrThrow({ where: { id: frontendId } });
+
+  const task = registeredTask.task as Prisma.JsonObject;
+  const id = task.id as string;
+
+  // Update the backend with the rejection
+  await oasstApiClient.nackTask(id, reason);
+
+  // Send the results to the client.
+  res.status(200).json({});
+};
+
+export default handler;
diff --git a/website/src/pages/api/update_task.ts b/website/src/pages/api/update_task.ts
index c8760324..e8e21ca9 100644
--- a/website/src/pages/api/update_task.ts
+++ b/website/src/pages/api/update_task.ts
@@ -1,3 +1,4 @@
+import { Prisma } from "@prisma/client";
 import { getToken } from "next-auth/jwt";
 import { oasstApiClient } from "src/lib/oasst_api_client";
 import prisma from "src/lib/prismadb";
@@ -6,9 +7,11 @@ import prisma from "src/lib/prismadb";
  * Stores the task interaction with the Task Backend and then returns the next task generated.
  *
  * This implicity does a few things:
- * 1) Stores the answer with the Task Backend.
- * 2) Records the new task in our local database.
- * 3) Returns the newly created task to the client.
+ * 1) Records the users answer in our local database.
+ * 2) Accepts the task.
+ * 3) Sends the users answer to the Task Backend.
+ * 4) Records the new task in our local database.
+ * 5) Returns the newly created task to the client.
  */
 const handler = async (req, res) => {
   const token = await getToken({ req });
@@ -20,7 +23,13 @@ const handler = async (req, res) => {
   }
 
   // Parse out the local task ID and the interaction contents.
-  const { id, content, update_type } = await JSON.parse(req.body);
+  const { id: frontendId, content, update_type } = await JSON.parse(req.body);
+
+  // Accept the task so that we can complete it, this will probably go away soon.
+  const registeredTask = await prisma.registeredTask.findUniqueOrThrow({ where: { id: frontendId } });
+  const task = registeredTask.task as Prisma.JsonObject;
+  const id = task.id as string;
+  await oasstApiClient.ackTask(id, registeredTask.id);
 
   // Log the interaction locally to create our user_post_id needed by the Task
   // Backend.
@@ -29,7 +38,7 @@ const handler = async (req, res) => {
       content,
       task: {
         connect: {
-          id,
+          id: frontendId,
         },
       },
     },
@@ -37,7 +46,7 @@ const handler = async (req, res) => {
 
   let newTask;
   try {
-    newTask = await oasstApiClient.interactTask(update_type, id, interaction.id, content, token);
+    newTask = await oasstApiClient.interactTask(update_type, frontendId, interaction.id, content, token);
   } catch (err) {
     return res.status(500).json(err);
   }
diff --git a/website/src/pages/create/summarize_story.tsx b/website/src/pages/create/summarize_story.tsx
index 1c5b89b9..8620a8f5 100644
--- a/website/src/pages/create/summarize_story.tsx
+++ b/website/src/pages/create/summarize_story.tsx
@@ -87,7 +87,12 @@ const SummarizeStory = () => {
           </>
         </TwoColumnsWithCards>
 
-        <TaskControls tasks={tasks} onSubmitResponse={submitResponse} onSkip={fetchNextTask} />
+        <TaskControls
+          tasks={tasks}
+          onSubmitResponse={submitResponse}
+          onSkipTask={fetchNextTask}
+          onNextTask={fetchNextTask}
+        />
       </main>
     </div>
   );
diff --git a/website/src/pages/evaluate/rate_summary.tsx b/website/src/pages/evaluate/rate_summary.tsx
index e0118ece..0d2352a2 100644
--- a/website/src/pages/evaluate/rate_summary.tsx
+++ b/website/src/pages/evaluate/rate_summary.tsx
@@ -102,7 +102,12 @@ const RateSummary = () => {
           </section>
         </TwoColumnsWithCards>
 
-        <TaskControls tasks={tasks} onSubmitResponse={submitResponse} onSkip={fetchNextTask} />
+        <TaskControls
+          tasks={tasks}
+          onSubmitResponse={submitResponse}
+          onSkipTask={fetchNextTask}
+          onNextTask={fetchNextTask}
+        />
       </main>
     </>
   );
diff --git a/website/src/pages/label/label_assistant_reply.tsx b/website/src/pages/label/label_assistant_reply.tsx
index d314a907..a0f961f7 100644
--- a/website/src/pages/label/label_assistant_reply.tsx
+++ b/website/src/pages/label/label_assistant_reply.tsx
@@ -33,7 +33,8 @@ const LabelAssistantReply = () => {
       controls={
         <TaskControls
           tasks={tasks}
-          onSkip={reset}
+          onSkipTask={() => reset()}
+          onNextTask={reset}
           onSubmitResponse={({ id, task }: LabelAssistantReplyTaskResponse) =>
             submit(id, task.message_id, task.reply, task.valid_labels, sliderValues)
           }
diff --git a/website/src/pages/label/label_initial_prompt.tsx b/website/src/pages/label/label_initial_prompt.tsx
index 7d1c606b..3c791f23 100644
--- a/website/src/pages/label/label_initial_prompt.tsx
+++ b/website/src/pages/label/label_initial_prompt.tsx
@@ -28,7 +28,8 @@ const LabelInitialPrompt = () => {
       controls={
         <TaskControls
           tasks={tasks}
-          onSkip={reset}
+          onSkipTask={() => reset()}
+          onNextTask={reset}
           onSubmitResponse={({ id, task }: LabelInitialPromptTaskResponse) =>
             submit(id, task.message_id, task.prompt, task.valid_labels, sliderValues)
           }
diff --git a/website/src/pages/label/label_prompter_reply.tsx b/website/src/pages/label/label_prompter_reply.tsx
index b5742b23..2fd3d76a 100644
--- a/website/src/pages/label/label_prompter_reply.tsx
+++ b/website/src/pages/label/label_prompter_reply.tsx
@@ -33,7 +33,8 @@ const LabelPrompterReply = () => {
       controls={
         <TaskControls
           tasks={tasks}
-          onSkip={reset}
+          onSkipTask={() => reset()}
+          onNextTask={reset}
           onSubmitResponse={({ id, task }: LabelPrompterReplyTaskResponse) =>
             submit(id, task.message_id, task.reply, task.valid_labels, sliderValues)
           }