diff --git a/hosting/docker-compose.yaml b/hosting/docker-compose.yaml
index 34cae92dc7..36b88466fe 100644
--- a/hosting/docker-compose.yaml
+++ b/hosting/docker-compose.yaml
@@ -26,7 +26,7 @@ services:
       BB_ADMIN_USER_EMAIL: ${BB_ADMIN_USER_EMAIL}
       BB_ADMIN_USER_PASSWORD: ${BB_ADMIN_USER_PASSWORD}
       PLUGINS_DIR: ${PLUGINS_DIR}
-      OFFLINE_MODE: ${OFFLINE_MODE}
+      OFFLINE_MODE: ${OFFLINE_MODE:-}
     depends_on:
       - worker-service
       - redis-service
@@ -53,7 +53,7 @@ services:
       INTERNAL_API_KEY: ${INTERNAL_API_KEY}
       REDIS_URL: redis-service:6379
       REDIS_PASSWORD: ${REDIS_PASSWORD}
-      OFFLINE_MODE: ${OFFLINE_MODE}
+      OFFLINE_MODE: ${OFFLINE_MODE:-}
     depends_on:
       - redis-service
       - minio-service
diff --git a/packages/backend-core/src/environment.ts b/packages/backend-core/src/environment.ts
index 138dbbd9e0..0fec786c31 100644
--- a/packages/backend-core/src/environment.ts
+++ b/packages/backend-core/src/environment.ts
@@ -166,6 +166,8 @@ const environment = {
   DISABLE_JWT_WARNING: process.env.DISABLE_JWT_WARNING,
   BLACKLIST_IPS: process.env.BLACKLIST_IPS,
   SERVICE_TYPE: "unknown",
+  PASSWORD_MIN_LENGTH: process.env.PASSWORD_MIN_LENGTH,
+  PASSWORD_MAX_LENGTH: process.env.PASSWORD_MAX_LENGTH,
   /**
    * Enable to allow an admin user to login using a password.
    * This can be useful to prevent lockout when configuring SSO.
diff --git a/packages/backend-core/src/middleware/authenticated.ts b/packages/backend-core/src/middleware/authenticated.ts
index 16f658b90a..e8e16589de 100644
--- a/packages/backend-core/src/middleware/authenticated.ts
+++ b/packages/backend-core/src/middleware/authenticated.ts
@@ -15,6 +15,7 @@ import * as identity from "../context/identity"
 import env from "../environment"
 import { Ctx, EndpointMatcher, SessionCookie } from "@budibase/types"
 import { InvalidAPIKeyError, ErrorCode } from "../errors"
+import tracer from "dd-trace"
 
 const ONE_MINUTE = env.SESSION_UPDATE_PERIOD
   ? parseInt(env.SESSION_UPDATE_PERIOD)
@@ -166,6 +167,19 @@ export default function (
       if (!authenticated) {
         authenticated = false
       }
+
+      if (user) {
+        tracer.setUser({
+          id: user?._id,
+          tenantId: user?.tenantId,
+          admin: user?.admin,
+          builder: user?.builder,
+          budibaseAccess: user?.budibaseAccess,
+          status: user?.status,
+          roles: user?.roles,
+        })
+      }
+
       // isAuthenticated is a function, so use a variable to be able to check authed state
       finalise(ctx, { authenticated, user, internal, version, publicEndpoint })
 
diff --git a/packages/backend-core/src/security/auth.ts b/packages/backend-core/src/security/auth.ts
index c90d9df09b..1cce35a0af 100644
--- a/packages/backend-core/src/security/auth.ts
+++ b/packages/backend-core/src/security/auth.ts
@@ -1,7 +1,7 @@
-import { env } from ".."
+import env from "../environment"
 
-export const PASSWORD_MIN_LENGTH = +(process.env.PASSWORD_MIN_LENGTH || 8)
-export const PASSWORD_MAX_LENGTH = +(process.env.PASSWORD_MAX_LENGTH || 512)
+export const PASSWORD_MIN_LENGTH = +(env.PASSWORD_MIN_LENGTH || 8)
+export const PASSWORD_MAX_LENGTH = +(env.PASSWORD_MAX_LENGTH || 512)
 
 export function validatePassword(
   password: string
diff --git a/packages/backend-core/src/users/db.ts b/packages/backend-core/src/users/db.ts
index 3214b3ab63..4d0d216603 100644
--- a/packages/backend-core/src/users/db.ts
+++ b/packages/backend-core/src/users/db.ts
@@ -44,6 +44,12 @@ type GroupFns = {
   getBulk: GroupGetFn
   getGroupBuilderAppIds: GroupBuildersFn
 }
+type CreateAdminUserOpts = {
+  ssoId?: string
+  hashPassword?: boolean
+  requirePassword?: boolean
+  skipPasswordValidation?: boolean
+}
 type FeatureFns = { isSSOEnforced: FeatureFn; isAppBuildersEnabled: FeatureFn }
 
 const bulkDeleteProcessing = async (dbUser: User) => {
@@ -112,9 +118,11 @@ export class UserDB {
         throw new HTTPError("Password change is disabled for this user", 400)
       }
 
-      const passwordValidation = validatePassword(password)
-      if (!passwordValidation.valid) {
-        throw new HTTPError(passwordValidation.error, 400)
+      if (!opts.skipPasswordValidation) {
+        const passwordValidation = validatePassword(password)
+        if (!passwordValidation.valid) {
+          throw new HTTPError(passwordValidation.error, 400)
+        }
       }
 
       hashedPassword = opts.hashPassword ? await hash(password) : password
@@ -489,7 +497,7 @@ export class UserDB {
     email: string,
     password: string,
     tenantId: string,
-    opts?: { ssoId?: string; hashPassword?: boolean; requirePassword?: boolean }
+    opts?: CreateAdminUserOpts
   ) {
     const user: User = {
       email: email,
@@ -513,6 +521,7 @@ export class UserDB {
     return await UserDB.save(user, {
       hashPassword: opts?.hashPassword,
       requirePassword: opts?.requirePassword,
+      skipPasswordValidation: opts?.skipPasswordValidation,
     })
   }
 
diff --git a/packages/server/src/startup.ts b/packages/server/src/startup.ts
index 6860fe5f9b..f9b5974eb2 100644
--- a/packages/server/src/startup.ts
+++ b/packages/server/src/startup.ts
@@ -138,7 +138,11 @@ export async function startup(app?: Koa, server?: Server) {
             bbAdminEmail,
             bbAdminPassword,
             tenantId,
-            { hashPassword: true, requirePassword: true }
+            {
+              hashPassword: true,
+              requirePassword: true,
+              skipPasswordValidation: true,
+            }
           )
           // Need to set up an API key for automated integration tests
           if (env.isTest()) {
diff --git a/packages/types/src/sdk/user.ts b/packages/types/src/sdk/user.ts
index 2b970da1a9..3f6f69d2d1 100644
--- a/packages/types/src/sdk/user.ts
+++ b/packages/types/src/sdk/user.ts
@@ -2,4 +2,5 @@ export interface SaveUserOpts {
   hashPassword?: boolean
   requirePassword?: boolean
   currentUserId?: string
+  skipPasswordValidation?: boolean
 }