diff --git a/overseerr-api.yml b/overseerr-api.yml
index 6bf7f69b7..6eaef6ba0 100644
--- a/overseerr-api.yml
+++ b/overseerr-api.yml
@@ -4430,7 +4430,16 @@ paths:
           schema:
             type: string
             nullable: true
-            enum: [all, approved, available, pending, processing, unavailable]
+            enum:
+              [
+                all,
+                approved,
+                available,
+                pending,
+                processing,
+                unavailable,
+                failed,
+              ]
         - in: query
           name: sort
           schema:
diff --git a/server/constants/media.ts b/server/constants/media.ts
index d9ef9e022..de2bf834d 100644
--- a/server/constants/media.ts
+++ b/server/constants/media.ts
@@ -2,6 +2,7 @@ export enum MediaRequestStatus {
   PENDING = 1,
   APPROVED,
   DECLINED,
+  FAILED,
 }
 
 export enum MediaType {
diff --git a/server/entity/MediaRequest.ts b/server/entity/MediaRequest.ts
index 3420c46d3..da19d0d4d 100644
--- a/server/entity/MediaRequest.ts
+++ b/server/entity/MediaRequest.ts
@@ -451,10 +451,13 @@ export class MediaRequest {
             await mediaRepository.save(media);
           })
           .catch(async () => {
-            media[this.is4k ? 'status4k' : 'status'] = MediaStatus.UNKNOWN;
-            await mediaRepository.save(media);
+            const requestRepository = getRepository(MediaRequest);
+
+            this.status = MediaRequestStatus.FAILED;
+            requestRepository.save(this);
+
             logger.warn(
-              'Something went wrong sending movie request to Radarr, marking status as UNKNOWN',
+              'Something went wrong sending movie request to Radarr, marking status as FAILED',
               {
                 label: 'Media Request',
                 requestId: this.id,
@@ -684,10 +687,13 @@ export class MediaRequest {
             await mediaRepository.save(media);
           })
           .catch(async () => {
-            media[this.is4k ? 'status4k' : 'status'] = MediaStatus.UNKNOWN;
-            await mediaRepository.save(media);
+            const requestRepository = getRepository(MediaRequest);
+
+            this.status = MediaRequestStatus.FAILED;
+            requestRepository.save(this);
+
             logger.warn(
-              'Something went wrong sending series request to Sonarr, marking status as UNKNOWN',
+              'Something went wrong sending series request to Sonarr, marking status as FAILED',
               {
                 label: 'Media Request',
                 requestId: this.id,
diff --git a/server/routes/request.ts b/server/routes/request.ts
index a8ad189d5..68d252547 100644
--- a/server/routes/request.ts
+++ b/server/routes/request.ts
@@ -40,11 +40,15 @@ requestRoutes.get<Record<string, unknown>, RequestResultsResponse>(
             MediaRequestStatus.APPROVED,
           ];
           break;
+        case 'failed':
+          statusFilter = [MediaRequestStatus.FAILED];
+          break;
         default:
           statusFilter = [
             MediaRequestStatus.PENDING,
             MediaRequestStatus.APPROVED,
             MediaRequestStatus.DECLINED,
+            MediaRequestStatus.FAILED,
           ];
       }
 
diff --git a/src/components/RequestBlock/index.tsx b/src/components/RequestBlock/index.tsx
index c20b8f25c..7521a5f1c 100644
--- a/src/components/RequestBlock/index.tsx
+++ b/src/components/RequestBlock/index.tsx
@@ -179,6 +179,11 @@ const RequestBlock = ({ request, onUpdate }: RequestBlockProps) => {
                   {intl.formatMessage(globalMessages.pending)}
                 </Badge>
               )}
+              {request.status === MediaRequestStatus.FAILED && (
+                <Badge badgeType="danger">
+                  {intl.formatMessage(globalMessages.failed)}
+                </Badge>
+              )}
             </div>
           </div>
           <div className="mt-2 flex items-center text-sm leading-5 sm:mt-0">
diff --git a/src/components/RequestButton/index.tsx b/src/components/RequestButton/index.tsx
index 8117d7bee..417acd846 100644
--- a/src/components/RequestButton/index.tsx
+++ b/src/components/RequestButton/index.tsx
@@ -77,13 +77,13 @@ const RequestButton = ({
     (request) => request.status === MediaRequestStatus.PENDING && request.is4k
   );
 
+  // Current user's pending request, or the first pending request
   const activeRequest = useMemo(() => {
     return activeRequests && activeRequests.length > 0
       ? activeRequests.find((request) => request.requestedBy.id === user?.id) ??
           activeRequests[0]
       : undefined;
   }, [activeRequests, user]);
-
   const active4kRequest = useMemo(() => {
     return active4kRequests && active4kRequests.length > 0
       ? active4kRequests.find(
@@ -121,6 +121,151 @@ const RequestButton = ({
   };
 
   const buttons: ButtonOption[] = [];
+
+  // If there are pending requests, show request management options first
+  if (activeRequest || active4kRequest) {
+    if (
+      activeRequest &&
+      (activeRequest.requestedBy.id === user?.id ||
+        (activeRequests?.length === 1 &&
+          hasPermission(Permission.MANAGE_REQUESTS)))
+    ) {
+      buttons.push({
+        id: 'active-request',
+        text: intl.formatMessage(messages.viewrequest),
+        action: () => {
+          setEditRequest(true);
+          setShowRequestModal(true);
+        },
+        svg: <InformationCircleIcon />,
+      });
+    }
+
+    if (
+      activeRequest &&
+      hasPermission(Permission.MANAGE_REQUESTS) &&
+      mediaType === 'movie'
+    ) {
+      buttons.push(
+        {
+          id: 'approve-request',
+          text: intl.formatMessage(messages.approverequest),
+          action: () => {
+            modifyRequest(activeRequest, 'approve');
+          },
+          svg: <CheckIcon />,
+        },
+        {
+          id: 'decline-request',
+          text: intl.formatMessage(messages.declinerequest),
+          action: () => {
+            modifyRequest(activeRequest, 'decline');
+          },
+          svg: <XIcon />,
+        }
+      );
+    } else if (
+      activeRequests &&
+      activeRequests.length > 0 &&
+      hasPermission(Permission.MANAGE_REQUESTS) &&
+      mediaType === 'tv'
+    ) {
+      buttons.push(
+        {
+          id: 'approve-request-batch',
+          text: intl.formatMessage(messages.approverequests, {
+            requestCount: activeRequests.length,
+          }),
+          action: () => {
+            modifyRequests(activeRequests, 'approve');
+          },
+          svg: <CheckIcon />,
+        },
+        {
+          id: 'decline-request-batch',
+          text: intl.formatMessage(messages.declinerequests, {
+            requestCount: activeRequests.length,
+          }),
+          action: () => {
+            modifyRequests(activeRequests, 'decline');
+          },
+          svg: <XIcon />,
+        }
+      );
+    }
+
+    if (
+      active4kRequest &&
+      (active4kRequest.requestedBy.id === user?.id ||
+        (active4kRequests?.length === 1 &&
+          hasPermission(Permission.MANAGE_REQUESTS)))
+    ) {
+      buttons.push({
+        id: 'active-4k-request',
+        text: intl.formatMessage(messages.viewrequest4k),
+        action: () => {
+          setEditRequest(true);
+          setShowRequest4kModal(true);
+        },
+        svg: <InformationCircleIcon />,
+      });
+    }
+
+    if (
+      active4kRequest &&
+      hasPermission(Permission.MANAGE_REQUESTS) &&
+      mediaType === 'movie'
+    ) {
+      buttons.push(
+        {
+          id: 'approve-4k-request',
+          text: intl.formatMessage(messages.approverequest4k),
+          action: () => {
+            modifyRequest(active4kRequest, 'approve');
+          },
+          svg: <CheckIcon />,
+        },
+        {
+          id: 'decline-4k-request',
+          text: intl.formatMessage(messages.declinerequest4k),
+          action: () => {
+            modifyRequest(active4kRequest, 'decline');
+          },
+          svg: <XIcon />,
+        }
+      );
+    } else if (
+      active4kRequests &&
+      active4kRequests.length > 0 &&
+      hasPermission(Permission.MANAGE_REQUESTS) &&
+      mediaType === 'tv'
+    ) {
+      buttons.push(
+        {
+          id: 'approve-4k-request-batch',
+          text: intl.formatMessage(messages.approve4krequests, {
+            requestCount: active4kRequests.length,
+          }),
+          action: () => {
+            modifyRequests(active4kRequests, 'approve');
+          },
+          svg: <CheckIcon />,
+        },
+        {
+          id: 'decline-4k-request-batch',
+          text: intl.formatMessage(messages.decline4krequests, {
+            requestCount: active4kRequests.length,
+          }),
+          action: () => {
+            modifyRequests(active4kRequests, 'decline');
+          },
+          svg: <XIcon />,
+        }
+      );
+    }
+  }
+
+  // Standard request button
   if (
     (!media || media.status === MediaStatus.UNKNOWN) &&
     hasPermission(
@@ -142,8 +287,29 @@ const RequestButton = ({
       },
       svg: <DownloadIcon />,
     });
+  } else if (
+    mediaType === 'tv' &&
+    (!activeRequest || activeRequest.requestedBy.id !== user?.id) &&
+    hasPermission([Permission.REQUEST, Permission.REQUEST_TV], {
+      type: 'or',
+    }) &&
+    media &&
+    media.status !== MediaStatus.AVAILABLE &&
+    media.status !== MediaStatus.UNKNOWN &&
+    !isShowComplete
+  ) {
+    buttons.push({
+      id: 'request-more',
+      text: intl.formatMessage(messages.requestmore),
+      action: () => {
+        setEditRequest(false);
+        setShowRequestModal(true);
+      },
+      svg: <DownloadIcon />,
+    });
   }
 
+  // 4K request button
   if (
     (!media || media.status4k === MediaStatus.UNKNOWN) &&
     hasPermission(
@@ -167,175 +333,7 @@ const RequestButton = ({
       },
       svg: <DownloadIcon />,
     });
-  }
-
-  if (
-    activeRequest &&
-    (activeRequest.requestedBy.id === user?.id ||
-      (activeRequests?.length === 1 &&
-        hasPermission(Permission.MANAGE_REQUESTS)))
-  ) {
-    buttons.push({
-      id: 'active-request',
-      text: intl.formatMessage(messages.viewrequest),
-      action: () => {
-        setEditRequest(true);
-        setShowRequestModal(true);
-      },
-      svg: <InformationCircleIcon />,
-    });
-  }
-
-  if (
-    active4kRequest &&
-    (active4kRequest.requestedBy.id === user?.id ||
-      (active4kRequests?.length === 1 &&
-        hasPermission(Permission.MANAGE_REQUESTS)))
-  ) {
-    buttons.push({
-      id: 'active-4k-request',
-      text: intl.formatMessage(messages.viewrequest4k),
-      action: () => {
-        setEditRequest(true);
-        setShowRequest4kModal(true);
-      },
-      svg: <InformationCircleIcon />,
-    });
-  }
-
-  if (
-    activeRequest &&
-    hasPermission(Permission.MANAGE_REQUESTS) &&
-    mediaType === 'movie'
-  ) {
-    buttons.push(
-      {
-        id: 'approve-request',
-        text: intl.formatMessage(messages.approverequest),
-        action: () => {
-          modifyRequest(activeRequest, 'approve');
-        },
-        svg: <CheckIcon />,
-      },
-      {
-        id: 'decline-request',
-        text: intl.formatMessage(messages.declinerequest),
-        action: () => {
-          modifyRequest(activeRequest, 'decline');
-        },
-        svg: <XIcon />,
-      }
-    );
-  }
-
-  if (
-    activeRequests &&
-    activeRequests.length > 0 &&
-    hasPermission(Permission.MANAGE_REQUESTS) &&
-    mediaType === 'tv'
-  ) {
-    buttons.push(
-      {
-        id: 'approve-request-batch',
-        text: intl.formatMessage(messages.approverequests, {
-          requestCount: activeRequests.length,
-        }),
-        action: () => {
-          modifyRequests(activeRequests, 'approve');
-        },
-        svg: <CheckIcon />,
-      },
-      {
-        id: 'decline-request-batch',
-        text: intl.formatMessage(messages.declinerequests, {
-          requestCount: activeRequests.length,
-        }),
-        action: () => {
-          modifyRequests(activeRequests, 'decline');
-        },
-        svg: <XIcon />,
-      }
-    );
-  }
-
-  if (
-    active4kRequest &&
-    hasPermission(Permission.MANAGE_REQUESTS) &&
-    mediaType === 'movie'
-  ) {
-    buttons.push(
-      {
-        id: 'approve-4k-request',
-        text: intl.formatMessage(messages.approverequest4k),
-        action: () => {
-          modifyRequest(active4kRequest, 'approve');
-        },
-        svg: <CheckIcon />,
-      },
-      {
-        id: 'decline-4k-request',
-        text: intl.formatMessage(messages.declinerequest4k),
-        action: () => {
-          modifyRequest(active4kRequest, 'decline');
-        },
-        svg: <XIcon />,
-      }
-    );
-  }
-
-  if (
-    active4kRequests &&
-    active4kRequests.length > 0 &&
-    hasPermission(Permission.MANAGE_REQUESTS) &&
-    mediaType === 'tv'
-  ) {
-    buttons.push(
-      {
-        id: 'approve-4k-request-batch',
-        text: intl.formatMessage(messages.approve4krequests, {
-          requestCount: active4kRequests.length,
-        }),
-        action: () => {
-          modifyRequests(active4kRequests, 'approve');
-        },
-        svg: <CheckIcon />,
-      },
-      {
-        id: 'decline-4k-request-batch',
-        text: intl.formatMessage(messages.decline4krequests, {
-          requestCount: active4kRequests.length,
-        }),
-        action: () => {
-          modifyRequests(active4kRequests, 'decline');
-        },
-        svg: <XIcon />,
-      }
-    );
-  }
-
-  if (
-    mediaType === 'tv' &&
-    (!activeRequest || activeRequest.requestedBy.id !== user?.id) &&
-    hasPermission([Permission.REQUEST, Permission.REQUEST_TV], {
-      type: 'or',
-    }) &&
-    media &&
-    media.status !== MediaStatus.AVAILABLE &&
-    media.status !== MediaStatus.UNKNOWN &&
-    !isShowComplete
-  ) {
-    buttons.push({
-      id: 'request-more',
-      text: intl.formatMessage(messages.requestmore),
-      action: () => {
-        setEditRequest(false);
-        setShowRequestModal(true);
-      },
-      svg: <DownloadIcon />,
-    });
-  }
-
-  if (
+  } else if (
     mediaType === 'tv' &&
     (!active4kRequest || active4kRequest.requestedBy.id !== user?.id) &&
     hasPermission([Permission.REQUEST_4K, Permission.REQUEST_4K_TV], {
diff --git a/src/components/RequestCard/index.tsx b/src/components/RequestCard/index.tsx
index 53f7b6841..bbeaa8bd5 100644
--- a/src/components/RequestCard/index.tsx
+++ b/src/components/RequestCard/index.tsx
@@ -12,10 +12,7 @@ import { useInView } from 'react-intersection-observer';
 import { defineMessages, useIntl } from 'react-intl';
 import { useToasts } from 'react-toast-notifications';
 import useSWR, { mutate } from 'swr';
-import {
-  MediaRequestStatus,
-  MediaStatus,
-} from '../../../server/constants/media';
+import { MediaRequestStatus } from '../../../server/constants/media';
 import type { MediaRequest } from '../../../server/entity/MediaRequest';
 import type { MovieDetails } from '../../../server/models/Movie';
 import type { TvDetails } from '../../../server/models/Tv';
@@ -275,8 +272,7 @@ const RequestCard = ({ request, onTitleData }: RequestCardProps) => {
               <Badge badgeType="danger">
                 {intl.formatMessage(globalMessages.declined)}
               </Badge>
-            ) : requestData.media[requestData.is4k ? 'status4k' : 'status'] ===
-              MediaStatus.UNKNOWN ? (
+            ) : requestData.status === MediaRequestStatus.FAILED ? (
               <Badge
                 badgeType="danger"
                 href={`/${requestData.type}/${requestData.media.tmdbId}?manage=1`}
@@ -305,9 +301,7 @@ const RequestCard = ({ request, onTitleData }: RequestCardProps) => {
             )}
           </div>
           <div className="flex flex-1 items-end space-x-2">
-            {requestData.media[requestData.is4k ? 'status4k' : 'status'] ===
-              MediaStatus.UNKNOWN &&
-              requestData.status !== MediaRequestStatus.DECLINED &&
+            {requestData.status === MediaRequestStatus.FAILED &&
               hasPermission(Permission.MANAGE_REQUESTS) && (
                 <Button
                   buttonType="primary"
diff --git a/src/components/RequestList/RequestItem/index.tsx b/src/components/RequestList/RequestItem/index.tsx
index f52279f31..14530b4a9 100644
--- a/src/components/RequestList/RequestItem/index.tsx
+++ b/src/components/RequestList/RequestItem/index.tsx
@@ -12,10 +12,7 @@ import { useInView } from 'react-intersection-observer';
 import { defineMessages, FormattedRelativeTime, useIntl } from 'react-intl';
 import { useToasts } from 'react-toast-notifications';
 import useSWR from 'swr';
-import {
-  MediaRequestStatus,
-  MediaStatus,
-} from '../../../../server/constants/media';
+import { MediaRequestStatus } from '../../../../server/constants/media';
 import type { MediaRequest } from '../../../../server/entity/MediaRequest';
 import type { MovieDetails } from '../../../../server/models/Movie';
 import type { TvDetails } from '../../../../server/models/Tv';
@@ -273,9 +270,7 @@ const RequestItem = ({ request, revalidateList }: RequestItemProps) => {
                 <Badge badgeType="danger">
                   {intl.formatMessage(globalMessages.declined)}
                 </Badge>
-              ) : requestData.media[
-                  requestData.is4k ? 'status4k' : 'status'
-                ] === MediaStatus.UNKNOWN ? (
+              ) : requestData.status === MediaRequestStatus.FAILED ? (
                 <Badge
                   badgeType="danger"
                   href={`/${requestData.type}/${requestData.media.tmdbId}?manage=1`}
@@ -402,9 +397,7 @@ const RequestItem = ({ request, revalidateList }: RequestItemProps) => {
           </div>
         </div>
         <div className="z-10 mt-4 flex w-full flex-col justify-center space-y-2 pl-4 pr-4 xl:mt-0 xl:w-96 xl:items-end xl:pl-0">
-          {requestData.media[requestData.is4k ? 'status4k' : 'status'] ===
-            MediaStatus.UNKNOWN &&
-            requestData.status !== MediaRequestStatus.DECLINED &&
+          {requestData.status === MediaRequestStatus.FAILED &&
             hasPermission(Permission.MANAGE_REQUESTS) && (
               <Button
                 className="w-full"
diff --git a/src/components/RequestList/index.tsx b/src/components/RequestList/index.tsx
index efef868a4..448f67964 100644
--- a/src/components/RequestList/index.tsx
+++ b/src/components/RequestList/index.tsx
@@ -33,6 +33,7 @@ enum Filter {
   PROCESSING = 'processing',
   AVAILABLE = 'available',
   UNAVAILABLE = 'unavailable',
+  FAILED = 'failed',
 }
 
 type Sort = 'added' | 'modified';
@@ -158,6 +159,9 @@ const RequestList = () => {
               <option value="processing">
                 {intl.formatMessage(globalMessages.processing)}
               </option>
+              <option value="failed">
+                {intl.formatMessage(globalMessages.failed)}
+              </option>
               <option value="available">
                 {intl.formatMessage(globalMessages.available)}
               </option>