diff --git a/Dockerfile b/Dockerfile
index fe2e0059..4a8e87aa 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -14,7 +14,10 @@ RUN apk update && \
     apk add --no-cache --update \
     curl \
     tzdata \
-    ffmpeg
+    ffmpeg \
+    make \
+    python3 \
+    g++
 
 COPY --from=tone /usr/local/bin/tone /usr/local/bin/
 COPY --from=build /client/dist /client/dist
@@ -23,6 +26,8 @@ COPY server server
 
 RUN npm ci --only=production
 
+RUN apk del make python3 g++
+
 EXPOSE 80
 HEALTHCHECK \
     --interval=30s \
diff --git a/client/components/cards/LazyBookCard.vue b/client/components/cards/LazyBookCard.vue
index b323c820..8b86dad0 100644
--- a/client/components/cards/LazyBookCard.vue
+++ b/client/components/cards/LazyBookCard.vue
@@ -756,6 +756,8 @@ export default {
       this.store.commit('globals/setConfirmPrompt', payload)
     },
     removeSeriesFromContinueListening() {
+      if (!this.series) return
+
       const axios = this.$axios || this.$nuxt.$axios
       this.processing = true
       axios
diff --git a/server/Database.js b/server/Database.js
index e5e06fee..56632a6b 100644
--- a/server/Database.js
+++ b/server/Database.js
@@ -236,7 +236,7 @@ class Database {
     if (newCollection) {
       const collectionBooks = []
       oldCollection.books.forEach((libraryItemId) => {
-        const libraryItem = this.libraryItems.filter(li => li.id === libraryItemId)
+        const libraryItem = this.libraryItems.find(li => li.id === libraryItemId)
         if (libraryItem) {
           collectionBooks.push({
             collectionId: newCollection.id,
diff --git a/server/Server.js b/server/Server.js
index 3afd03d9..3d80e773 100644
--- a/server/Server.js
+++ b/server/Server.js
@@ -230,10 +230,10 @@ class Server {
   async initializeServer(req, res) {
     Logger.info(`[Server] Initializing new server`)
     const newRoot = req.body.newRoot
-    let rootPash = newRoot.password ? await this.auth.hashPass(newRoot.password) : ''
+    const rootUsername = newRoot.username || 'root'
+    const rootPash = newRoot.password ? await this.auth.hashPass(newRoot.password) : ''
     if (!rootPash) Logger.warn(`[Server] Creating root user with no password`)
-    let rootToken = await this.auth.generateAccessToken({ userId: 'root', username: newRoot.username })
-    await Database.createRootUser(newRoot.username, rootPash, rootToken)
+    await Database.createRootUser(rootUsername, rootPash, this.auth)
 
     res.sendStatus(200)
   }
diff --git a/server/controllers/LibraryController.js b/server/controllers/LibraryController.js
index 8bc38db7..5b2819b4 100644
--- a/server/controllers/LibraryController.js
+++ b/server/controllers/LibraryController.js
@@ -43,7 +43,8 @@ class LibraryController {
     }
 
     const library = new Library()
-    newLibraryPayload.displayOrder = Database.libraries.length + 1
+
+    newLibraryPayload.displayOrder = Database.libraries.map(li => li.displayOrder).sort((a, b) => a - b).pop() + 1
     library.setData(newLibraryPayload)
     await Database.createLibrary(library)
 
diff --git a/server/controllers/MiscController.js b/server/controllers/MiscController.js
index cd7f12d5..0ed7ef8f 100644
--- a/server/controllers/MiscController.js
+++ b/server/controllers/MiscController.js
@@ -112,19 +112,19 @@ class MiscController {
       Logger.error('User other than admin attempting to update server settings', req.user)
       return res.sendStatus(403)
     }
-    var settingsUpdate = req.body
+    const settingsUpdate = req.body
     if (!settingsUpdate || !isObject(settingsUpdate)) {
       return res.status(500).send('Invalid settings update object')
     }
 
-    var madeUpdates = Database.serverSettings.update(settingsUpdate)
+    const madeUpdates = Database.serverSettings.update(settingsUpdate)
     if (madeUpdates) {
+      await Database.updateServerSettings()
+
       // If backup schedule is updated - update backup manager
       if (settingsUpdate.backupSchedule !== undefined) {
         this.backupManager.updateCronSchedule()
       }
-
-      await Database.updateServerSettings()
     }
     return res.json({
       success: true,
diff --git a/server/managers/EmailManager.js b/server/managers/EmailManager.js
index 14106d72..1298b5b5 100644
--- a/server/managers/EmailManager.js
+++ b/server/managers/EmailManager.js
@@ -1,4 +1,5 @@
 const nodemailer = require('nodemailer')
+const Database = require('../Database')
 const Logger = require("../Logger")
 
 class EmailManager {
diff --git a/server/managers/PlaybackSessionManager.js b/server/managers/PlaybackSessionManager.js
index 0794d508..05151672 100644
--- a/server/managers/PlaybackSessionManager.js
+++ b/server/managers/PlaybackSessionManager.js
@@ -52,6 +52,7 @@ class PlaybackSessionManager {
       }
     }
 
+    await Database.createDevice(deviceInfo)
 
     return deviceInfo
   }
@@ -221,9 +222,6 @@ class PlaybackSessionManager {
       newPlaybackSession.audioTracks = audioTracks
     }
 
-    // Will save on the first sync
-    user.currentSessionId = newPlaybackSession.id
-
     this.sessions.push(newPlaybackSession)
     SocketAuthority.adminEmitter('user_stream_update', user.toJSONForPublic(this.sessions, Database.libraryItems))
 
diff --git a/server/models/Author.js b/server/models/Author.js
index b100bbd8..8626e27c 100644
--- a/server/models/Author.js
+++ b/server/models/Author.js
@@ -77,7 +77,9 @@ module.exports = (sequelize) => {
   })
 
   const { library } = sequelize.models
-  library.hasMany(Author)
+  library.hasMany(Author, {
+    onDelete: 'CASCADE'
+  })
   Author.belongsTo(library)
 
   return Author
diff --git a/server/models/CollectionBook.js b/server/models/CollectionBook.js
index 0312e0be..16ab70c0 100644
--- a/server/models/CollectionBook.js
+++ b/server/models/CollectionBook.js
@@ -32,10 +32,14 @@ module.exports = (sequelize) => {
   book.belongsToMany(collection, { through: CollectionBook })
   collection.belongsToMany(book, { through: CollectionBook })
 
-  book.hasMany(CollectionBook)
+  book.hasMany(CollectionBook, {
+    onDelete: 'CASCADE'
+  })
   CollectionBook.belongsTo(book)
 
-  collection.hasMany(CollectionBook)
+  collection.hasMany(CollectionBook, {
+    onDelete: 'CASCADE'
+  })
   CollectionBook.belongsTo(collection)
 
   return CollectionBook
diff --git a/server/models/Device.js b/server/models/Device.js
index cde4ce7f..a8917c19 100644
--- a/server/models/Device.js
+++ b/server/models/Device.js
@@ -32,7 +32,9 @@ module.exports = (sequelize) => {
 
     static async getOldDeviceByDeviceId(deviceId) {
       const device = await this.findOne({
-        deviceId
+        where: {
+          deviceId
+        }
       })
       if (!device) return null
       return device.getOldDevice()
@@ -105,7 +107,9 @@ module.exports = (sequelize) => {
 
   const { user } = sequelize.models
 
-  user.hasMany(Device)
+  user.hasMany(Device, {
+    onDelete: 'CASCADE'
+  })
   Device.belongsTo(user)
 
   return Device
diff --git a/server/models/FeedEpisode.js b/server/models/FeedEpisode.js
index 405ab211..2525b664 100644
--- a/server/models/FeedEpisode.js
+++ b/server/models/FeedEpisode.js
@@ -73,7 +73,9 @@ module.exports = (sequelize) => {
 
   const { feed } = sequelize.models
 
-  feed.hasMany(FeedEpisode)
+  feed.hasMany(FeedEpisode, {
+    onDelete: 'CASCADE'
+  })
   FeedEpisode.belongsTo(feed)
 
   return FeedEpisode
diff --git a/server/models/Library.js b/server/models/Library.js
index 6c8e8261..6fee9ad6 100644
--- a/server/models/Library.js
+++ b/server/models/Library.js
@@ -39,18 +39,19 @@ module.exports = (sequelize) => {
      * @param {object} oldLibrary 
      * @returns {Library|null}
      */
-    static createFromOld(oldLibrary) {
+    static async createFromOld(oldLibrary) {
       const library = this.getFromOld(oldLibrary)
 
       library.libraryFolders = oldLibrary.folders.map(folder => {
         return {
           id: folder.id,
-          path: folder.fullPath,
-          libraryId: library.id
+          path: folder.fullPath
         }
       })
 
-      return this.create(library).catch((error) => {
+      return this.create(library, {
+        include: sequelize.models.libraryFolder
+      }).catch((error) => {
         Logger.error(`[Library] Failed to create library ${library.id}`, error)
         return null
       })
diff --git a/server/models/LibraryFolder.js b/server/models/LibraryFolder.js
index 537947f3..6578dcde 100644
--- a/server/models/LibraryFolder.js
+++ b/server/models/LibraryFolder.js
@@ -16,7 +16,9 @@ module.exports = (sequelize) => {
   })
 
   const { library } = sequelize.models
-  library.hasMany(LibraryFolder)
+  library.hasMany(LibraryFolder, {
+    onDelete: 'CASCADE'
+  })
   LibraryFolder.belongsTo(library)
 
   return LibraryFolder
diff --git a/server/models/MediaProgress.js b/server/models/MediaProgress.js
index 913f46ec..d21085d2 100644
--- a/server/models/MediaProgress.js
+++ b/server/models/MediaProgress.js
@@ -134,7 +134,9 @@ module.exports = (sequelize) => {
     }
   })
 
-  user.hasMany(MediaProgress)
+  user.hasMany(MediaProgress, {
+    onDelete: 'CASCADE'
+  })
   MediaProgress.belongsTo(user)
 
   return MediaProgress
diff --git a/server/models/PlaylistMediaItem.js b/server/models/PlaylistMediaItem.js
index 7d2960e8..915739e6 100644
--- a/server/models/PlaylistMediaItem.js
+++ b/server/models/PlaylistMediaItem.js
@@ -75,7 +75,9 @@ module.exports = (sequelize) => {
     }
   })
 
-  playlist.hasMany(PlaylistMediaItem)
+  playlist.hasMany(PlaylistMediaItem, {
+    onDelete: 'CASCADE'
+  })
   PlaylistMediaItem.belongsTo(playlist)
 
   return PlaylistMediaItem
diff --git a/server/models/Series.js b/server/models/Series.js
index 85519b98..b71f3e9d 100644
--- a/server/models/Series.js
+++ b/server/models/Series.js
@@ -71,7 +71,9 @@ module.exports = (sequelize) => {
   })
 
   const { library } = sequelize.models
-  library.hasMany(Series)
+  library.hasMany(Series, {
+    onDelete: 'CASCADE'
+  })
   Series.belongsTo(library)
 
   return Series
diff --git a/server/models/User.js b/server/models/User.js
index e7656310..32b2b436 100644
--- a/server/models/User.js
+++ b/server/models/User.js
@@ -89,9 +89,13 @@ module.exports = (sequelize) => {
       })
     }
 
-    static async createRootUser(username, pash, token) {
+    static async createRootUser(username, pash, auth) {
+      const userId = uuidv4()
+
+      const token = await auth.generateAccessToken({ userId, username })
+
       const newRoot = new oldUser({
-        id: uuidv4(),
+        id: userId,
         type: 'root',
         username,
         pash,
diff --git a/server/objects/DeviceInfo.js b/server/objects/DeviceInfo.js
index 2f7438cc..ceff6c32 100644
--- a/server/objects/DeviceInfo.js
+++ b/server/objects/DeviceInfo.js
@@ -90,7 +90,7 @@ class DeviceInfo {
   setData(ip, ua, clientDeviceInfo, serverVersion, userId) {
     this.id = uuidv4()
     this.userId = userId
-    this.deviceId = clientDeviceInfo?.deviceId || null
+    this.deviceId = clientDeviceInfo?.deviceId || this.id
     this.ipAddress = ip || null
 
     this.browserName = ua?.browser.name || null
diff --git a/server/utils/migrations/dbMigration.js b/server/utils/migrations/dbMigration.js
index 676f2344..35877fb6 100644
--- a/server/utils/migrations/dbMigration.js
+++ b/server/utils/migrations/dbMigration.js
@@ -432,7 +432,11 @@ function migrateUsers(oldUsers) {
 
 function migrateSessions(oldSessions) {
   for (const oldSession of oldSessions) {
-    const userId = oldDbIdMap.users[oldSession.userId] || null // Can be null
+    const userId = oldDbIdMap.users[oldSession.userId]
+    if (!userId) {
+      Logger.debug(`[dbMigration] Not migrating playback session ${oldSession.id} because user was not found`)
+      continue
+    }
 
     //
     // Migrate Device