diff --git a/server/entity/MediaRequest.ts b/server/entity/MediaRequest.ts
index 3cf653e35..0cef4b1b6 100644
--- a/server/entity/MediaRequest.ts
+++ b/server/entity/MediaRequest.ts
@@ -34,11 +34,16 @@ export class QuotaRestrictedError extends Error {}
 export class DuplicateMediaRequestError extends Error {}
 export class NoSeasonsAvailableError extends Error {}
 
+type MediaRequestOptions = {
+  isAutoRequest?: boolean;
+};
+
 @Entity()
 export class MediaRequest {
   public static async request(
     requestBody: MediaRequestBody,
-    user: User
+    user: User,
+    options: MediaRequestOptions = {}
   ): Promise<MediaRequest> {
     const tmdb = new TheMovieDb();
     const mediaRepository = getRepository(Media);
@@ -140,21 +145,23 @@ export class MediaRequest {
       }
     }
 
-    if (requestBody.mediaType === MediaType.MOVIE) {
-      const existing = await requestRepository
-        .createQueryBuilder('request')
-        .leftJoin('request.media', 'media')
-        .where('request.is4k = :is4k', { is4k: requestBody.is4k })
-        .andWhere('media.tmdbId = :tmdbId', { tmdbId: tmdbMedia.id })
-        .andWhere('media.mediaType = :mediaType', {
-          mediaType: MediaType.MOVIE,
-        })
-        .andWhere('request.status != :requestStatus', {
-          requestStatus: MediaRequestStatus.DECLINED,
-        })
-        .getOne();
-
-      if (existing) {
+    const existing = await requestRepository
+      .createQueryBuilder('request')
+      .leftJoin('request.media', 'media')
+      .leftJoinAndSelect('request.requestedBy', 'user')
+      .where('request.is4k = :is4k', { is4k: requestBody.is4k })
+      .andWhere('media.tmdbId = :tmdbId', { tmdbId: tmdbMedia.id })
+      .andWhere('media.mediaType = :mediaType', {
+        mediaType: requestBody.mediaType,
+      })
+      .getMany();
+
+    if (existing && existing.length > 0) {
+      // If there is an existing movie request that isn't declined, don't allow a new one.
+      if (
+        requestBody.mediaType === MediaType.MOVIE &&
+        existing[0].status !== MediaRequestStatus.DECLINED
+      ) {
         logger.warn('Duplicate request for media blocked', {
           tmdbId: tmdbMedia.id,
           mediaType: requestBody.mediaType,
@@ -167,6 +174,20 @@ export class MediaRequest {
         );
       }
 
+      // If an existing auto-request for this media exists from the same user,
+      // don't allow a new one.
+      if (
+        existing.find(
+          (r) => r.requestedBy.id === requestUser.id && r.isAutoRequest
+        )
+      ) {
+        throw new DuplicateMediaRequestError(
+          'Auto-request for this media and user already exists.'
+        );
+      }
+    }
+
+    if (requestBody.mediaType === MediaType.MOVIE) {
       await mediaRepository.save(media);
 
       const request = new MediaRequest({
@@ -207,6 +228,7 @@ export class MediaRequest {
         profileId: requestBody.profileId,
         rootFolder: requestBody.rootFolder,
         tags: requestBody.tags,
+        isAutoRequest: options.isAutoRequest ?? false,
       });
 
       await requestRepository.save(request);
@@ -330,6 +352,7 @@ export class MediaRequest {
                 : MediaRequestStatus.PENDING,
             })
         ),
+        isAutoRequest: options.isAutoRequest ?? false,
       });
 
       await requestRepository.save(request);
@@ -427,6 +450,9 @@ export class MediaRequest {
   })
   public tags?: number[];
 
+  @Column({ default: false })
+  public isAutoRequest: boolean;
+
   constructor(init?: Partial<MediaRequest>) {
     Object.assign(this, init);
   }
diff --git a/server/lib/watchlistsync.ts b/server/lib/watchlistsync.ts
index c1092f54e..40eddf55c 100644
--- a/server/lib/watchlistsync.ts
+++ b/server/lib/watchlistsync.ts
@@ -121,7 +121,8 @@ class WatchlistSync {
               tvdbId: mediaItem.tvdbId,
               is4k: false,
             },
-            user
+            user,
+            { isAutoRequest: true }
           );
         } catch (e) {
           if (!(e instanceof Error)) {
diff --git a/server/migration/1660714479373-AddMediaRequestIsAutoRequestedField.ts b/server/migration/1660714479373-AddMediaRequestIsAutoRequestedField.ts
new file mode 100644
index 000000000..8580bb4ed
--- /dev/null
+++ b/server/migration/1660714479373-AddMediaRequestIsAutoRequestedField.ts
@@ -0,0 +1,33 @@
+import type { MigrationInterface, QueryRunner } from 'typeorm';
+
+export class AddMediaRequestIsAutoRequestedField1660714479373
+  implements MigrationInterface
+{
+  name = 'AddMediaRequestIsAutoRequestedField1660714479373';
+
+  public async up(queryRunner: QueryRunner): Promise<void> {
+    await queryRunner.query(
+      `CREATE TABLE "temporary_media_request" ("id" integer PRIMARY KEY AUTOINCREMENT NOT NULL, "status" integer NOT NULL, "createdAt" datetime NOT NULL DEFAULT (datetime('now')), "updatedAt" datetime NOT NULL DEFAULT (datetime('now')), "type" varchar NOT NULL, "mediaId" integer, "requestedById" integer, "modifiedById" integer, "is4k" boolean NOT NULL DEFAULT (0), "serverId" integer, "profileId" integer, "rootFolder" varchar, "languageProfileId" integer, "tags" text, "isAutoRequest" boolean NOT NULL DEFAULT (0), CONSTRAINT "FK_a1aa713f41c99e9d10c48da75a0" FOREIGN KEY ("mediaId") REFERENCES "media" ("id") ON DELETE CASCADE ON UPDATE NO ACTION, CONSTRAINT "FK_6997bee94720f1ecb7f31137095" FOREIGN KEY ("requestedById") REFERENCES "user" ("id") ON DELETE CASCADE ON UPDATE NO ACTION, CONSTRAINT "FK_f4fc4efa14c3ba2b29c4525fa15" FOREIGN KEY ("modifiedById") REFERENCES "user" ("id") ON DELETE SET NULL ON UPDATE NO ACTION)`
+    );
+    await queryRunner.query(
+      `INSERT INTO "temporary_media_request"("id", "status", "createdAt", "updatedAt", "type", "mediaId", "requestedById", "modifiedById", "is4k", "serverId", "profileId", "rootFolder", "languageProfileId", "tags") SELECT "id", "status", "createdAt", "updatedAt", "type", "mediaId", "requestedById", "modifiedById", "is4k", "serverId", "profileId", "rootFolder", "languageProfileId", "tags" FROM "media_request"`
+    );
+    await queryRunner.query(`DROP TABLE "media_request"`);
+    await queryRunner.query(
+      `ALTER TABLE "temporary_media_request" RENAME TO "media_request"`
+    );
+  }
+
+  public async down(queryRunner: QueryRunner): Promise<void> {
+    await queryRunner.query(
+      `ALTER TABLE "media_request" RENAME TO "temporary_media_request"`
+    );
+    await queryRunner.query(
+      `CREATE TABLE "media_request" ("id" integer PRIMARY KEY AUTOINCREMENT NOT NULL, "status" integer NOT NULL, "createdAt" datetime NOT NULL DEFAULT (datetime('now')), "updatedAt" datetime NOT NULL DEFAULT (datetime('now')), "type" varchar NOT NULL, "mediaId" integer, "requestedById" integer, "modifiedById" integer, "is4k" boolean NOT NULL DEFAULT (0), "serverId" integer, "profileId" integer, "rootFolder" varchar, "languageProfileId" integer, "tags" text, CONSTRAINT "FK_a1aa713f41c99e9d10c48da75a0" FOREIGN KEY ("mediaId") REFERENCES "media" ("id") ON DELETE CASCADE ON UPDATE NO ACTION, CONSTRAINT "FK_6997bee94720f1ecb7f31137095" FOREIGN KEY ("requestedById") REFERENCES "user" ("id") ON DELETE CASCADE ON UPDATE NO ACTION, CONSTRAINT "FK_f4fc4efa14c3ba2b29c4525fa15" FOREIGN KEY ("modifiedById") REFERENCES "user" ("id") ON DELETE SET NULL ON UPDATE NO ACTION)`
+    );
+    await queryRunner.query(
+      `INSERT INTO "media_request"("id", "status", "createdAt", "updatedAt", "type", "mediaId", "requestedById", "modifiedById", "is4k", "serverId", "profileId", "rootFolder", "languageProfileId", "tags") SELECT "id", "status", "createdAt", "updatedAt", "type", "mediaId", "requestedById", "modifiedById", "is4k", "serverId", "profileId", "rootFolder", "languageProfileId", "tags" FROM "temporary_media_request"`
+    );
+    await queryRunner.query(`DROP TABLE "temporary_media_request"`);
+  }
+}