diff --git a/src/backend/common/Cache.ts b/src/backend/common/Cache.ts
index 51aa5a03..a1f19189 100644
--- a/src/backend/common/Cache.ts
+++ b/src/backend/common/Cache.ts
@@ -13,7 +13,8 @@ import { childLogger, Logger } from '@foxxmd/logging';
 import { projectDir } from './index.js';
 import path from 'path';
 import { cacheFunctions } from "@foxxmd/regex-buddy-core";
-import { fileOrDirectoryIsWriteable } from '../utils/FSUtils.js';
+import { fileExists, fileOrDirectoryIsWriteable } from '../utils/FSUtils.js';
+import { copyFile } from 'fs/promises';
 import { asCacheAuthProvider, asCacheConfig, asCacheMetadataProvider, asCacheScrobbleProvider, CacheAuthProvider, CacheConfig, CacheConfigOptions, CacheMetadataProvider, CacheProvider, CacheScrobbleProvider } from './infrastructure/Atomic.js';
 import { Typeson } from 'typeson';
 import { builtin } from 'typeson-registry';
@@ -384,6 +385,12 @@ export const flatCacheLoad = async (flatCache: FlatCache, logger: Logger = logge
         throw new Error(`Unable to use path for file cache at ${cachePath}`, { cause: e })
     }
 
+    if(fileExists(cachePath) && !fileExists(`${cachePath}.bak`)) {
+        logger.info(`Backing up ${cachePath} in preparation for migration to database...`);
+        await copyFile(cachePath, `${cachePath}.bak`);
+        logger.info(`Done! Backed up to ${cachePath}.bak\nAll data has been loaded into cache. It will be deleted (from cache) after migrating to database.\nIf there are migration issues or you wish to downgrade then overwrite ${cachePath} with the .bak backup copy`);
+    }
+
     const streamPromise = new Promise((resolve, reject) => {
         flatCache.loadFileStream(cachePath, (progress: number, total: number) => {
             logger.trace(`Loading ${progress}/${total} chunks...`);
diff --git a/src/backend/scrobblers/AbstractScrobbleClient.ts b/src/backend/scrobblers/AbstractScrobbleClient.ts
index 5a31e444..ec4d5e87 100644
--- a/src/backend/scrobblers/AbstractScrobbleClient.ts
+++ b/src/backend/scrobblers/AbstractScrobbleClient.ts
@@ -449,14 +449,95 @@ export default abstract class AbstractScrobbleClient extends AbstractComponent i
 
     protected async doParseCache(): Promise<true | string | undefined> {
         const cachedQueue = (await this.cache.cacheScrobble.get(`${this.getMachineId()}-queue`) as QueuedScrobble<PlayObject>[] ?? []);
-        const cachedQLength = cachedQueue.length;
-        //this.queuedScrobbles = cachedQueue.map(x => ({...x, play: rehydratePlay(x.play)}));
+        if (cachedQueue.length > 0) {
+            this.logger.info('Migrating cached scrobbles to database...');
+            let allGood = true;
+            for (const cachedQueuedScrobble of cachedQueue) {
+                const play = asPlay(cachedQueuedScrobble.play);
+                const {
+                    meta: {
+                        lifecycle,
+                        ...metaRest
+                    },
+                } = play;
+                try {
+                    const res = await this.playRepo.createPlays([
+                        playToRepositoryCreatePlayOpts({
+                            play: {
+                                ...play,
+                                meta: {
+                                    ...metaRest,
+                                    lifecycle: {
+                                        steps: []
+                                    }
+                                }
+                            },
+                            componentId: this.dbComponent.id,
+                            state: 'queued',
+                            parentId: play.id
+                        })
+                    ]);
+                    this.logger.verbose(`Migrated Play ${res[0].uid} => ${buildTrackString(play)}`);
+                } catch (e) {
+                    allGood = false;
+                    this.logger.verbose(new Error(`Failed to migrate Play ${buildTrackString(play)}`, {cause: e}));
+                }
+            }
+            this.logger[allGood ? 'info' : 'warn'](allGood ? 'Finished migrating all queued scrobbles.' : 'Migrated queued scrobbles with errors');
+            await this.cache.cacheScrobble.delete(`${this.getMachineId()}-queue`);
+            this.logger.info('Deleted legacy cached queued scrobbles');
+        }
 
         const cachedDead = (await this.cache.cacheScrobble.get(`${this.getMachineId()}-dead`) as DeadLetterScrobble<PlayObject>[] ?? []);
-        const cachedDLength = cachedDead.length;
-        //this.deadLetterScrobbles = cachedDead.map(x => ({...x, play: rehydratePlay(x.play), lastRetry: x.lastRetry !== undefined ? dayjs(x.lastRetry) : undefined}));
+        if(cachedDead.length > 0) {
+            this.logger.info('Migrating failed scrobbles to database...');
+            let allGood = true;
+            for(const cDeadScrobble of cachedDead) {
+                const play = asPlay(cDeadScrobble.play);
+                const {
+                    meta: {
+                        lifecycle,
+                        ...metaRest
+                    },
+                } = play;
+                try {
+                    const res = await this.playRepo.createPlays([
+                        playToRepositoryCreatePlayOpts({
+                            play: {
+                                ...play,
+                                meta: {
+                                    ...metaRest,
+                                    lifecycle: {
+                                        steps: []
+                                    }
+                                }
+                            },
+                            componentId: this.dbComponent.id,
+                            state: 'failed',
+                            parentId: play.id
+                        })
+                    ]);
+                    this.logger.verbose(`Added Play ${res[0].uid} to database => ${buildTrackString(play)}`);
+                    await this.queueRepo.create({
+                        componentId: this.dbComponent.id,
+                        playId: res[0].id,
+                        queueName: CLIENT_DEAD_QUEUE,
+                        queueStatus: 'queued',
+                        retries: cDeadScrobble.retries,
+                        error: cDeadScrobble.error !== undefined ? {message: cDeadScrobble.error } : undefined
+                    });
+                    this.logger.verbose(`Added Play ${res[0].uid} to Failed Queue`);
+                } catch (e) {
+                    allGood = false;
+                    this.logger.verbose(new Error(`Failed to migrate Play to failed queued ${buildTrackString(play)}`, {cause: e}));
+                }
+                this.logger[allGood ? 'info' : 'warn'](allGood ? 'Finished migrating all failed scrobbles.' : 'Migrated failed scrobbles with errors');
+                await this.cache.cacheScrobble.delete(`${this.getMachineId()}-dead`);
+                this.logger.info('Deleted legacy cached failed scrobbles');
+            }
+        }
 
-        return `Scrobbles from Cache: ${cachedQLength} Queue | ${cachedDLength} Dead Letter`;
+        return;
     }
 
     protected async postInitialize(): Promise<void> {