diff --git a/server/Auth.js b/server/Auth.js
index 1d229ceb..55eb334a 100644
--- a/server/Auth.js
+++ b/server/Auth.js
@@ -63,13 +63,6 @@ class Auth {
     return passport.authenticate('jwt', { session: false })(req, res, next)
   }
 
-  /**
-   * Generate a token which is used to encrpt/protect the jwts.
-   */
-  async initTokenSecret() {
-    return this.tokenManager.initTokenSecret()
-  }
-
   /**
    * Function to generate a jwt token for a given user
    * TODO: Old method with no expiration
@@ -132,7 +125,7 @@ class Auth {
       new JwtStrategy(
         {
           jwtFromRequest: ExtractJwt.fromExtractors([ExtractJwt.fromAuthHeaderAsBearerToken(), ExtractJwt.fromUrlQueryParameter('token')]),
-          secretOrKey: Database.serverSettings.tokenSecret,
+          secretOrKey: TokenManager.TokenSecret,
           // Handle expiration manaully in order to disable api keys that are expired
           ignoreExpiration: true
         },
diff --git a/server/Server.js b/server/Server.js
index cf0ad5c7..99e72d0c 100644
--- a/server/Server.js
+++ b/server/Server.js
@@ -156,14 +156,11 @@ class Server {
     }
 
     await Database.init(false)
+    // Create or set JWT secret in token manager
+    await this.auth.tokenManager.initTokenSecret()
 
     await Logger.logManager.init()
 
-    // Create token secret if does not exist (Added v2.1.0)
-    if (!Database.serverSettings.tokenSecret) {
-      await this.auth.initTokenSecret()
-    }
-
     await this.cleanUserData() // Remove invalid user item progress
     await CacheManager.ensureCachePaths()
 
@@ -264,7 +261,7 @@ class Server {
     // enable express-session
     app.use(
       expressSession({
-        secret: global.ServerSettings.tokenSecret,
+        secret: this.auth.tokenManager.TokenSecret,
         resave: false,
         saveUninitialized: false,
         cookie: {
diff --git a/server/auth/TokenManager.js b/server/auth/TokenManager.js
index cc4783b5..3f5cc836 100644
--- a/server/auth/TokenManager.js
+++ b/server/auth/TokenManager.js
@@ -7,8 +7,13 @@ const requestIp = require('../libs/requestIp')
 const jwt = require('../libs/jsonwebtoken')
 
 class TokenManager {
+  /** @type {string} JWT secret key */
+  static TokenSecret = null
+
   constructor() {
+    /** @type {number} Refresh token expiry in seconds */
     this.RefreshTokenExpiry = parseInt(process.env.REFRESH_TOKEN_EXPIRY) || 7 * 24 * 60 * 60 // 7 days
+    /** @type {number} Access token expiry in seconds */
     this.AccessTokenExpiry = parseInt(process.env.ACCESS_TOKEN_EXPIRY) || 12 * 60 * 60 // 12 hours
 
     if (parseInt(process.env.REFRESH_TOKEN_EXPIRY) > 0) {
@@ -19,28 +24,28 @@ class TokenManager {
     }
   }
 
+  get TokenSecret() {
+    return TokenManager.TokenSecret
+  }
+
   /**
-   * Generate a token which is used to encrypt/protect the jwts.
+   * Token secret is used to sign and verify JWTs
+   * Set by ENV variable "JWT_SECRET_KEY" or generated and stored on server settings if not set
    */
   async initTokenSecret() {
-    if (process.env.TOKEN_SECRET) {
-      // User can supply their own token secret
-      Database.serverSettings.tokenSecret = process.env.TOKEN_SECRET
+    if (process.env.JWT_SECRET_KEY) {
+      // Use user supplied token secret
+      Logger.info('[TokenManager] JWT secret key set from ENV variable')
+      TokenManager.TokenSecret = process.env.JWT_SECRET_KEY
+    } else if (!Database.serverSettings.tokenSecret) {
+      // Generate new token secret and store it on server settings
+      Logger.info('[TokenManager] JWT secret key not found, generating one')
+      TokenManager.TokenSecret = require('crypto').randomBytes(256).toString('base64')
+      Database.serverSettings.tokenSecret = TokenManager.TokenSecret
+      await Database.updateServerSettings()
     } else {
-      Database.serverSettings.tokenSecret = require('crypto').randomBytes(256).toString('base64')
-    }
-    await Database.updateServerSettings()
-
-    // TODO: Old method of non-expiring tokens
-    // New token secret creation added in v2.1.0 so generate new API tokens for each user
-    const users = await Database.userModel.findAll({
-      attributes: ['id', 'username', 'token']
-    })
-    if (users.length) {
-      for (const user of users) {
-        user.token = this.generateAccessToken(user)
-        await user.save({ hooks: false })
-      }
+      // Use existing token secret from server settings
+      TokenManager.TokenSecret = Database.serverSettings.tokenSecret
     }
   }
 
@@ -70,7 +75,7 @@ class TokenManager {
    */
   static validateAccessToken(token) {
     try {
-      return jwt.verify(token, global.ServerSettings.tokenSecret)
+      return jwt.verify(token, TokenManager.TokenSecret)
     } catch (err) {
       return null
     }
@@ -85,7 +90,7 @@ class TokenManager {
    * @returns {string}
    */
   generateAccessToken(user) {
-    return jwt.sign({ userId: user.id, username: user.username }, global.ServerSettings.tokenSecret)
+    return jwt.sign({ userId: user.id, username: user.username }, TokenManager.TokenSecret)
   }
 
   /**
@@ -104,7 +109,7 @@ class TokenManager {
       expiresIn: this.AccessTokenExpiry
     }
     try {
-      return jwt.sign(payload, global.ServerSettings.tokenSecret, options)
+      return jwt.sign(payload, TokenManager.TokenSecret, options)
     } catch (error) {
       Logger.error(`[TokenManager] Error generating access token for user ${user.id}: ${error}`)
       return null
@@ -127,7 +132,7 @@ class TokenManager {
       expiresIn: this.RefreshTokenExpiry
     }
     try {
-      return jwt.sign(payload, global.ServerSettings.tokenSecret, options)
+      return jwt.sign(payload, TokenManager.TokenSecret, options)
     } catch (error) {
       Logger.error(`[TokenManager] Error generating refresh token for user ${user.id}: ${error}`)
       return null
@@ -261,7 +266,7 @@ class TokenManager {
   async handleRefreshToken(refreshToken, req, res) {
     try {
       // Verify the refresh token
-      const decoded = jwt.verify(refreshToken, global.ServerSettings.tokenSecret)
+      const decoded = jwt.verify(refreshToken, TokenManager.TokenSecret)
 
       if (decoded.type !== 'refresh') {
         Logger.error(`[TokenManager] Failed to refresh token. Invalid token type: ${decoded.type}`)
diff --git a/server/controllers/ApiKeyController.js b/server/controllers/ApiKeyController.js
index f60480df..c09d0736 100644
--- a/server/controllers/ApiKeyController.js
+++ b/server/controllers/ApiKeyController.js
@@ -42,6 +42,8 @@ class ApiKeyController {
   /**
    * POST: /api/api-keys
    *
+   * @this {import('../routers/ApiRouter')}
+   *
    * @param {RequestWithUser} req
    * @param {Response} res
    */
@@ -69,7 +71,7 @@ class ApiKeyController {
     }
 
     const keyId = uuidv4() // Generate key id ahead of time to use in JWT
-    const apiKey = await Database.apiKeyModel.generateApiKey(keyId, req.body.name, req.body.expiresIn)
+    const apiKey = await Database.apiKeyModel.generateApiKey(this.auth.tokenManager.TokenSecret, keyId, req.body.name, req.body.expiresIn)
 
     if (!apiKey) {
       Logger.error(`[ApiKeyController] create: Error generating API key`)
diff --git a/server/models/ApiKey.js b/server/models/ApiKey.js
index 7b61f731..7c61611d 100644
--- a/server/models/ApiKey.js
+++ b/server/models/ApiKey.js
@@ -157,12 +157,13 @@ class ApiKey extends Model {
 
   /**
    * Generate a new api key
+   * @param {string} tokenSecret
    * @param {string} keyId
    * @param {string} name
    * @param {number} [expiresIn] - Seconds until the api key expires or undefined for no expiration
    * @returns {Promise<string>}
    */
-  static async generateApiKey(keyId, name, expiresIn) {
+  static async generateApiKey(tokenSecret, keyId, name, expiresIn) {
     const options = {}
     if (expiresIn && !isNaN(expiresIn) && expiresIn > 0) {
       options.expiresIn = expiresIn
@@ -175,7 +176,7 @@ class ApiKey extends Model {
           name,
           type: 'api'
         },
-        global.ServerSettings.tokenSecret,
+        tokenSecret,
         options,
         (err, token) => {
           if (err) {
diff --git a/server/objects/settings/ServerSettings.js b/server/objects/settings/ServerSettings.js
index 29913e44..4f0aa97b 100644
--- a/server/objects/settings/ServerSettings.js
+++ b/server/objects/settings/ServerSettings.js
@@ -7,6 +7,7 @@ const User = require('../../models/User')
 class ServerSettings {
   constructor(settings) {
     this.id = 'server-settings'
+    /** @type {string} JWT secret key ONLY used when JWT_SECRET_KEY is not set in ENV */
     this.tokenSecret = null
 
     // Scanner