diff --git a/src/components/RequestBlock/index.tsx b/src/components/RequestBlock/index.tsx
index 5ea29c3d56..2355dcce50 100644
--- a/src/components/RequestBlock/index.tsx
+++ b/src/components/RequestBlock/index.tsx
@@ -7,6 +7,7 @@ import useRequestOverride from '@app/hooks/useRequestOverride';
 import { useUser } from '@app/hooks/useUser';
 import globalMessages from '@app/i18n/globalMessages';
 import defineMessages from '@app/utils/defineMessages';
+import { formatFailureReason } from '@app/utils/requestFailureHelpers';
 import {
   CalendarIcon,
   CheckIcon,
@@ -225,9 +226,17 @@ const RequestBlock = ({ request, onUpdate }: RequestBlockProps) => {
                 </Badge>
               )}
               {request.status === MediaRequestStatus.FAILED && (
-                <Badge badgeType="danger">
-                  {intl.formatMessage(globalMessages.failed)}
-                </Badge>
+                <Tooltip
+                  content={formatFailureReason(
+                    intl,
+                    request.type,
+                    request.failureReason
+                  )}
+                >
+                  <Badge badgeType="danger">
+                    {intl.formatMessage(globalMessages.failed)}
+                  </Badge>
+                </Tooltip>
               )}
               {request.status === MediaRequestStatus.COMPLETED && (
                 <Badge badgeType="success">
diff --git a/src/components/RequestCard/index.tsx b/src/components/RequestCard/index.tsx
index 0f2341f5ee..51b1b77902 100644
--- a/src/components/RequestCard/index.tsx
+++ b/src/components/RequestCard/index.tsx
@@ -14,10 +14,16 @@ import {
   getRequestDownloadStatus,
   refreshIntervalHelper,
 } from '@app/utils/refreshIntervalHelper';
+import {
+  canRetryRequest,
+  canSearchAnotherListing,
+  formatFailureReason,
+} from '@app/utils/requestFailureHelpers';
 import { withProperties } from '@app/utils/typeHelpers';
 import {
   ArrowPathIcon,
   CheckIcon,
+  MagnifyingGlassIcon,
   PencilIcon,
   TrashIcon,
   XMarkIcon,
@@ -149,11 +155,19 @@ const RequestCardError = ({ requestData }: RequestCardErrorProps) => {
                   </span>
                   {requestData.status === MediaRequestStatus.DECLINED ||
                   requestData.status === MediaRequestStatus.FAILED ? (
-                    <Badge badgeType="danger">
-                      {requestData.status === MediaRequestStatus.DECLINED
-                        ? intl.formatMessage(globalMessages.declined)
-                        : intl.formatMessage(globalMessages.failed)}
-                    </Badge>
+                    <Tooltip
+                      content={formatFailureReason(
+                        intl,
+                        requestData.type,
+                        requestData.failureReason
+                      )}
+                    >
+                      <Badge badgeType="danger">
+                        {requestData.status === MediaRequestStatus.DECLINED
+                          ? intl.formatMessage(globalMessages.declined)
+                          : intl.formatMessage(globalMessages.failed)}
+                      </Badge>
+                    </Tooltip>
                   ) : (
                     <StatusBadge
                       status={
@@ -442,12 +456,20 @@ const RequestCard = ({ request, onTitleData }: RequestCardProps) => {
                 {intl.formatMessage(globalMessages.declined)}
               </Badge>
             ) : requestData.status === MediaRequestStatus.FAILED ? (
-              <Badge
-                badgeType="danger"
-                href={`/${requestData.type}/${requestData.media.tmdbId}?manage=1`}
+              <Tooltip
+                content={formatFailureReason(
+                  intl,
+                  requestData.type,
+                  requestData.failureReason
+                )}
               >
-                {intl.formatMessage(globalMessages.failed)}
-              </Badge>
+                <Badge
+                  badgeType="danger"
+                  href={`/${requestData.type}/${requestData.media.tmdbId}?manage=1`}
+                >
+                  {intl.formatMessage(globalMessages.failed)}
+                </Badge>
+              </Tooltip>
             ) : requestData.status === MediaRequestStatus.PENDING &&
               requestData.media[requestData.is4k ? 'status4k' : 'status'] ===
                 MediaStatus.DELETED ? (
@@ -480,20 +502,56 @@ const RequestCard = ({ request, onTitleData }: RequestCardProps) => {
           <div className="flex flex-1 items-end space-x-2">
             {requestData.status === MediaRequestStatus.FAILED &&
               hasPermission(Permission.MANAGE_REQUESTS) && (
-                <Button
-                  buttonType="primary"
-                  buttonSize="sm"
-                  disabled={isRetrying}
-                  onClick={() => retryRequest()}
+                <Tooltip
+                  content={
+                    canRetryRequest(requestData.failureReason)
+                      ? undefined
+                      : intl.formatMessage(globalMessages.retryunavailable)
+                  }
                 >
-                  <ArrowPathIcon
-                    className={isRetrying ? 'animate-spin' : ''}
-                    style={{ marginRight: '0', animationDirection: 'reverse' }}
-                  />
-                  <span className="ml-1.5 hidden sm:block">
-                    {intl.formatMessage(globalMessages.retry)}
-                  </span>
-                </Button>
+                  <Button
+                    buttonType="primary"
+                    buttonSize="sm"
+                    disabled={
+                      isRetrying || !canRetryRequest(requestData.failureReason)
+                    }
+                    onClick={() => retryRequest()}
+                  >
+                    <ArrowPathIcon
+                      className={isRetrying ? 'animate-spin' : ''}
+                      style={{
+                        marginRight: '0',
+                        animationDirection: 'reverse',
+                      }}
+                    />
+                    <span className="ml-1.5 hidden sm:block">
+                      {intl.formatMessage(globalMessages.retry)}
+                    </span>
+                  </Button>
+                </Tooltip>
+              )}
+            {requestData.status === MediaRequestStatus.FAILED &&
+              canSearchAnotherListing(requestData.failureReason) &&
+              title && (
+                <Link
+                  href={`/search?query=${encodeURIComponent(
+                    isMovie(title) ? title.title : title.name
+                  )}`}
+                  passHref
+                  legacyBehavior
+                >
+                  <Button
+                    as="a"
+                    buttonType="default"
+                    buttonSize="sm"
+                    title={intl.formatMessage(globalMessages.findlisting)}
+                  >
+                    <MagnifyingGlassIcon style={{ marginRight: '0' }} />
+                    <span className="ml-1.5 hidden sm:block">
+                      {intl.formatMessage(globalMessages.findlisting)}
+                    </span>
+                  </Button>
+                </Link>
               )}
             {requestData.status === MediaRequestStatus.PENDING &&
               hasPermission(Permission.MANAGE_REQUESTS) && (
diff --git a/src/components/RequestList/RequestItem/index.tsx b/src/components/RequestList/RequestItem/index.tsx
index 29a11ac514..cbcafed963 100644
--- a/src/components/RequestList/RequestItem/index.tsx
+++ b/src/components/RequestList/RequestItem/index.tsx
@@ -3,6 +3,7 @@ import Badge from '@app/components/Common/Badge';
 import Button from '@app/components/Common/Button';
 import CachedImage from '@app/components/Common/CachedImage';
 import ConfirmButton from '@app/components/Common/ConfirmButton';
+import Tooltip from '@app/components/Common/Tooltip';
 import RequestModal from '@app/components/RequestModal';
 import StatusBadge from '@app/components/StatusBadge';
 import useDeepLinks from '@app/hooks/useDeepLinks';
@@ -14,9 +15,15 @@ import {
   getRequestDownloadStatus,
   refreshIntervalHelper,
 } from '@app/utils/refreshIntervalHelper';
+import {
+  canRetryRequest,
+  canSearchAnotherListing,
+  formatFailureReason,
+} from '@app/utils/requestFailureHelpers';
 import {
   ArrowPathIcon,
   CheckIcon,
+  MagnifyingGlassIcon,
   PencilIcon,
   TrashIcon,
   XMarkIcon,
@@ -139,11 +146,19 @@ const RequestItemError = ({
                 </span>
                 {requestData.status === MediaRequestStatus.DECLINED ||
                 requestData.status === MediaRequestStatus.FAILED ? (
-                  <Badge badgeType="danger">
-                    {requestData.status === MediaRequestStatus.DECLINED
-                      ? intl.formatMessage(globalMessages.declined)
-                      : intl.formatMessage(globalMessages.failed)}
-                  </Badge>
+                  <Tooltip
+                    content={formatFailureReason(
+                      intl,
+                      requestData.type,
+                      requestData.failureReason
+                    )}
+                  >
+                    <Badge badgeType="danger">
+                      {requestData.status === MediaRequestStatus.DECLINED
+                        ? intl.formatMessage(globalMessages.declined)
+                        : intl.formatMessage(globalMessages.failed)}
+                    </Badge>
+                  </Tooltip>
                 ) : (
                   <StatusBadge
                     status={
@@ -527,12 +542,20 @@ const RequestItem = ({ request, revalidateList }: RequestItemProps) => {
                   {intl.formatMessage(globalMessages.declined)}
                 </Badge>
               ) : requestData.status === MediaRequestStatus.FAILED ? (
-                <Badge
-                  badgeType="danger"
-                  href={`/${requestData.type}/${requestData.media.tmdbId}?manage=1`}
+                <Tooltip
+                  content={formatFailureReason(
+                    intl,
+                    requestData.type,
+                    requestData.failureReason
+                  )}
                 >
-                  {intl.formatMessage(globalMessages.failed)}
-                </Badge>
+                  <Badge
+                    badgeType="danger"
+                    href={`/${requestData.type}/${requestData.media.tmdbId}?manage=1`}
+                  >
+                    {intl.formatMessage(globalMessages.failed)}
+                  </Badge>
+                </Tooltip>
               ) : requestData.status === MediaRequestStatus.PENDING &&
                 requestData.media[requestData.is4k ? 'status4k' : 'status'] ===
                   MediaStatus.DELETED ? (
@@ -683,22 +706,50 @@ const RequestItem = ({ request, revalidateList }: RequestItemProps) => {
         <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.status === MediaRequestStatus.FAILED &&
             hasPermission(Permission.MANAGE_REQUESTS) && (
-              <Button
-                className="w-full"
-                buttonType="primary"
-                disabled={isRetrying}
-                onClick={() => retryRequest()}
+              <Tooltip
+                content={
+                  canRetryRequest(requestData.failureReason)
+                    ? undefined
+                    : intl.formatMessage(globalMessages.retryunavailable)
+                }
               >
-                <ArrowPathIcon
-                  className={isRetrying ? 'animate-spin' : ''}
-                  style={{ animationDirection: 'reverse' }}
-                />
-                <span>
-                  {intl.formatMessage(
-                    isRetrying ? globalMessages.retrying : globalMessages.retry
-                  )}
-                </span>
-              </Button>
+                <Button
+                  className="w-full"
+                  buttonType="primary"
+                  disabled={
+                    isRetrying || !canRetryRequest(requestData.failureReason)
+                  }
+                  onClick={() => retryRequest()}
+                >
+                  <ArrowPathIcon
+                    className={isRetrying ? 'animate-spin' : ''}
+                    style={{ animationDirection: 'reverse' }}
+                  />
+                  <span>
+                    {intl.formatMessage(
+                      isRetrying
+                        ? globalMessages.retrying
+                        : globalMessages.retry
+                    )}
+                  </span>
+                </Button>
+              </Tooltip>
+            )}
+          {requestData.status === MediaRequestStatus.FAILED &&
+            canSearchAnotherListing(requestData.failureReason) &&
+            title && (
+              <Link
+                href={`/search?query=${encodeURIComponent(
+                  isMovie(title) ? title.title : title.name
+                )}`}
+                passHref
+                legacyBehavior
+              >
+                <Button as="a" className="w-full" buttonType="default">
+                  <MagnifyingGlassIcon />
+                  <span>{intl.formatMessage(globalMessages.findlisting)}</span>
+                </Button>
+              </Link>
             )}
           {requestData.status !== MediaRequestStatus.PENDING &&
             hasPermission(Permission.MANAGE_REQUESTS) && (
diff --git a/src/i18n/globalMessages.ts b/src/i18n/globalMessages.ts
index 51eac54508..b09414d582 100644
--- a/src/i18n/globalMessages.ts
+++ b/src/i18n/globalMessages.ts
@@ -73,6 +73,15 @@ const globalMessages = defineMessages('i18n', {
   removefromBlocklist: 'Remove from Blocklist',
   specials: 'Specials',
   notificationLocale: 'Notification Language',
+  findlisting: 'Find Listing',
+  retryunavailable: 'Retrying cannot resolve this failure.',
+  failurereasonunreachable: 'Could not connect to {serviceName}.',
+  failurereasondispatch: '{serviceName} rejected the request.',
+  failurereasontvdbid: 'This series could not be identified on TheTVDB.',
+  failurereasonseasonunverified:
+    'The season numbering could not be checked against TheTVDB.',
+  failurereasonseasonmismatch:
+    'This listing numbers its seasons differently than TheTVDB.',
 });
 
 export default globalMessages;
diff --git a/src/i18n/locale/en.json b/src/i18n/locale/en.json
index 9a2e9c78d1..8e076780f7 100644
--- a/src/i18n/locale/en.json
+++ b/src/i18n/locale/en.json
@@ -1665,6 +1665,12 @@
   "i18n.error": "Something went wrong. Please try again.",
   "i18n.experimental": "Experimental",
   "i18n.failed": "Failed",
+  "i18n.failurereasondispatch": "{serviceName} rejected the request.",
+  "i18n.failurereasonseasonmismatch": "This listing numbers its seasons differently than TheTVDB.",
+  "i18n.failurereasonseasonunverified": "The season numbering could not be checked against TheTVDB.",
+  "i18n.failurereasontvdbid": "This series could not be identified on TheTVDB.",
+  "i18n.failurereasonunreachable": "Could not connect to {serviceName}.",
+  "i18n.findlisting": "Find Listing",
   "i18n.import": "Import",
   "i18n.importing": "Importing…",
   "i18n.loading": "Loading…",
@@ -1691,6 +1697,7 @@
   "i18n.resultsperpage": "Display {pageSize} results per page",
   "i18n.retry": "Retry",
   "i18n.retrying": "Retrying…",
+  "i18n.retryunavailable": "Retrying cannot resolve this failure.",
   "i18n.save": "Save Changes",
   "i18n.saving": "Saving…",
   "i18n.settings": "Settings",
diff --git a/src/utils/requestFailureHelpers.ts b/src/utils/requestFailureHelpers.ts
new file mode 100644
index 0000000000..d341cb6d6f
--- /dev/null
+++ b/src/utils/requestFailureHelpers.ts
@@ -0,0 +1,42 @@
+import globalMessages from '@app/i18n/globalMessages';
+import { MediaRequestFailureReason, MediaType } from '@server/constants/media';
+import type { IntlShape, MessageDescriptor } from 'react-intl';
+
+const failureReasonMessages: Record<
+  MediaRequestFailureReason,
+  MessageDescriptor
+> = {
+  [MediaRequestFailureReason.SERVICE_UNREACHABLE]:
+    globalMessages.failurereasonunreachable,
+  [MediaRequestFailureReason.DISPATCH_FAILED]:
+    globalMessages.failurereasondispatch,
+  [MediaRequestFailureReason.TVDB_ID_UNRESOLVED]:
+    globalMessages.failurereasontvdbid,
+  [MediaRequestFailureReason.SEASON_NUMBERING_UNVERIFIED]:
+    globalMessages.failurereasonseasonunverified,
+  [MediaRequestFailureReason.SEASON_NUMBERING_MISMATCH]:
+    globalMessages.failurereasonseasonmismatch,
+};
+
+export const formatFailureReason = (
+  intl: IntlShape,
+  type: MediaType,
+  reason?: MediaRequestFailureReason | null
+): string | undefined => {
+  const message = reason ? failureReasonMessages[reason] : undefined;
+
+  return message
+    ? intl.formatMessage(message, {
+        serviceName: type === MediaType.MOVIE ? 'Radarr' : 'Sonarr',
+      })
+    : undefined;
+};
+
+export const canSearchAnotherListing = (
+  reason?: MediaRequestFailureReason | null
+): boolean => reason === MediaRequestFailureReason.SEASON_NUMBERING_MISMATCH;
+
+// a numbering mismatch re-runs the same comparison on every attempt
+export const canRetryRequest = (
+  reason?: MediaRequestFailureReason | null
+): boolean => reason !== MediaRequestFailureReason.SEASON_NUMBERING_MISMATCH;