diff --git a/server/routers/olm/error.ts b/server/routers/olm/error.ts
index 289e7219..6ea209ce 100644
--- a/server/routers/olm/error.ts
+++ b/server/routers/olm/error.ts
@@ -3,7 +3,7 @@ import { sendToClient } from "#dynamic/routers/ws";
 export const OlmErrorCodes = {
     OLM_NOT_FOUND: {
         code: "OLM_NOT_FOUND",
-        message: "The requested OLM session could not be found."
+        message: "The specified device could not be found."
     },
     CLIENT_ID_NOT_FOUND: {
         code: "CLIENT_ID_NOT_FOUND",
@@ -15,15 +15,18 @@ export const OlmErrorCodes = {
     },
     CLIENT_BLOCKED: {
         code: "CLIENT_BLOCKED",
-        message: "This client has been blocked and cannot connect."
+        message:
+            "This client has been blocked in this organization and cannot connect. Please contact your administrator."
     },
     CLIENT_PENDING: {
         code: "CLIENT_PENDING",
-        message: "This client is pending approval and cannot connect yet."
+        message:
+            "This client is pending approval and cannot connect yet. Please contact your administrator."
     },
     ORG_NOT_FOUND: {
         code: "ORG_NOT_FOUND",
-        message: "The organization could not be found."
+        message:
+            "The organization could not be found. Please select a valid organization."
     },
     USER_ID_NOT_FOUND: {
         code: "USER_ID_NOT_FOUND",
@@ -31,23 +34,42 @@ export const OlmErrorCodes = {
     },
     INVALID_USER_SESSION: {
         code: "INVALID_USER_SESSION",
-        message: "Your user session is invalid or has expired."
+        message:
+            "Your user session is invalid or has expired. Please log in again."
     },
     USER_ID_MISMATCH: {
         code: "USER_ID_MISMATCH",
         message: "The provided user ID does not match the session."
     },
-    ACCESS_POLICY_DENIED: {
-        code: "ACCESS_POLICY_DENIED",
-        message: "Access denied due to policy restrictions."
+    ORG_ACCESS_POLICY_DENIED: {
+        code: "ORG_ACCESS_POLICY_DENIED",
+        message:
+            "Access to this organization has been denied by policy. Please contact your administrator."
+    },
+    ORG_ACCESS_POLICY_PASSWORD_EXPIRED: {
+        code: "ORG_ACCESS_POLICY_PASSWORD_EXPIRED",
+        message:
+            "Access to this organization has been denied because your password has expired. Please visit this organization's dashboard to update your password."
+    },
+    ORG_ACCESS_POLICY_SESSION_EXPIRED: {
+        code: "ORG_ACCESS_POLICY_SESSION_EXPIRED",
+        message:
+            "Access to this organization has been denied because your session has expired. Please log in again to refresh the session."
+    },
+    ORG_ACCESS_POLICY_2FA_REQUIRED: {
+        code: "ORG_ACCESS_POLICY_2FA_REQUIRED",
+        message:
+            "Access to this organization requires two-factor authentication. Please visit this organization's dashboard to enable two-factor authentication."
     },
     TERMINATED_REKEYED: {
         code: "TERMINATED_REKEYED",
-        message: "This session was terminated because encryption keys were regenerated."
+        message:
+            "This session was terminated because encryption keys were regenerated."
     },
     TERMINATED_ORG_DELETED: {
         code: "TERMINATED_ORG_DELETED",
-        message: "This session was terminated because the organization was deleted."
+        message:
+            "This session was terminated because the organization was deleted."
     },
     TERMINATED_INACTIVITY: {
         code: "TERMINATED_INACTIVITY",
@@ -69,7 +91,7 @@ export const OlmErrorCodes = {
 
 // Helper function to send registration error
 export async function sendOlmError(
-    error: typeof OlmErrorCodes[keyof typeof OlmErrorCodes],
+    error: (typeof OlmErrorCodes)[keyof typeof OlmErrorCodes],
     olmId: string
 ) {
     sendToClient(olmId, {
diff --git a/server/routers/olm/handleOlmRegisterMessage.ts b/server/routers/olm/handleOlmRegisterMessage.ts
index a8c1327d..c8a8d3f7 100644
--- a/server/routers/olm/handleOlmRegisterMessage.ts
+++ b/server/routers/olm/handleOlmRegisterMessage.ts
@@ -1,29 +1,16 @@
-import {
-    Client,
-    clientPostureSnapshots,
-    clientSiteResourcesAssociationsCache,
-    db,
-    fingerprints,
-    orgs,
-    siteResources
-} from "@server/db";
+import { clientPostureSnapshots, db, fingerprints, orgs } from "@server/db";
 import { MessageHandler } from "@server/routers/ws";
 import {
     clients,
     clientSitesAssociationsCache,
-    exitNodes,
     Olm,
     olms,
     sites
 } from "@server/db";
-import { and, count, eq, inArray, isNull } from "drizzle-orm";
-import { addPeer, deletePeer } from "../newt/peers";
+import { count, eq } from "drizzle-orm";
 import logger from "@server/logger";
-import { generateAliasConfig } from "@server/lib/ip";
-import { generateRemoteSubnets } from "@server/lib/ip";
 import { checkOrgAccessPolicy } from "#dynamic/lib/checkOrgAccessPolicy";
 import { validateSessionToken } from "@server/auth/sessions/app";
-import config from "@server/lib/config";
 import { encodeHexLowerCase } from "@oslojs/encoding";
 import { sha256 } from "@oslojs/crypto/sha2";
 import { buildSiteConfigurationForOlmClient } from "./buildConfiguration";
@@ -54,10 +41,7 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
 
     if (!olm.clientId) {
         logger.warn("Olm client ID not found");
-        sendOlmError(
-            OlmErrorCodes.CLIENT_ID_NOT_FOUND,
-            olm.olmId
-        );
+        sendOlmError(OlmErrorCodes.CLIENT_ID_NOT_FOUND, olm.olmId);
         return;
     }
 
@@ -69,10 +53,7 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
 
     if (!client) {
         logger.warn("Client ID not found");
-        sendOlmError(
-            OlmErrorCodes.CLIENT_NOT_FOUND,
-            olm.olmId
-        );
+        sendOlmError(OlmErrorCodes.CLIENT_NOT_FOUND, olm.olmId);
         return;
     }
 
@@ -80,10 +61,7 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
         logger.debug(
             `Client ${client.clientId} is blocked. Ignoring register.`
         );
-        sendOlmError(
-            OlmErrorCodes.CLIENT_BLOCKED,
-            olm.olmId
-        );
+        sendOlmError(OlmErrorCodes.CLIENT_BLOCKED, olm.olmId);
         return;
     }
 
@@ -91,10 +69,7 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
         logger.debug(
             `Client ${client.clientId} approval is pending. Ignoring register.`
         );
-        sendOlmError(
-            OlmErrorCodes.CLIENT_PENDING,
-            olm.olmId
-        );
+        sendOlmError(OlmErrorCodes.CLIENT_PENDING, olm.olmId);
         return;
     }
 
@@ -106,20 +81,14 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
 
     if (!org) {
         logger.warn("Org not found");
-        sendOlmError(
-            OlmErrorCodes.ORG_NOT_FOUND,
-            olm.olmId
-        );
+        sendOlmError(OlmErrorCodes.ORG_NOT_FOUND, olm.olmId);
         return;
     }
 
     if (orgId) {
         if (!olm.userId) {
             logger.warn("Olm has no user ID");
-            sendOlmError(
-                OlmErrorCodes.USER_ID_NOT_FOUND,
-                olm.olmId
-            );
+            sendOlmError(OlmErrorCodes.USER_ID_NOT_FOUND, olm.olmId);
             return;
         }
 
@@ -127,18 +96,12 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
             await validateSessionToken(userToken);
         if (!userSession || !user) {
             logger.warn("Invalid user session for olm register");
-            sendOlmError(
-                OlmErrorCodes.INVALID_USER_SESSION,
-                olm.olmId
-            );
+            sendOlmError(OlmErrorCodes.INVALID_USER_SESSION, olm.olmId);
             return;
         }
         if (user.userId !== olm.userId) {
             logger.warn("User ID mismatch for olm register");
-            sendOlmError(
-                OlmErrorCodes.USER_ID_MISMATCH,
-                olm.olmId
-            );
+            sendOlmError(OlmErrorCodes.USER_ID_MISMATCH, olm.olmId);
             return;
         }
 
@@ -152,14 +115,46 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
             sessionId // this is the user token passed in the message
         });
 
-        if (!policyCheck.allowed) {
+        if (policyCheck?.error) {
+            logger.error(
+                `Error checking access policies for olm user ${olm.userId} in org ${orgId}: ${policyCheck?.error}`
+            );
+            sendOlmError(OlmErrorCodes.ORG_ACCESS_POLICY_DENIED, olm.olmId);
+            return;
+        }
+
+        if (policyCheck?.policies?.passwordAge?.compliant) {
+            logger.warn(
+                `Olm user ${olm.userId} has non-compliant password age for org ${orgId}`
+            );
+            sendOlmError(
+                OlmErrorCodes.ORG_ACCESS_POLICY_PASSWORD_EXPIRED,
+                olm.olmId
+            );
+            return;
+        } else if (policyCheck?.policies?.maxSessionLength?.compliant) {
+            logger.warn(
+                `Olm user ${olm.userId} has non-compliant session length for org ${orgId}`
+            );
+            sendOlmError(
+                OlmErrorCodes.ORG_ACCESS_POLICY_SESSION_EXPIRED,
+                olm.olmId
+            );
+            return;
+        } else if (policyCheck?.policies?.requiredTwoFactor) {
+            logger.warn(
+                `Olm user ${olm.userId} does not have 2FA enabled for org ${orgId}`
+            );
+            sendOlmError(
+                OlmErrorCodes.ORG_ACCESS_POLICY_2FA_REQUIRED,
+                olm.olmId
+            );
+            return;
+        } else if (!policyCheck.allowed) {
             logger.warn(
                 `Olm user ${olm.userId} does not pass access policies for org ${orgId}: ${policyCheck.error}`
             );
-            sendOlmError(
-                OlmErrorCodes.ACCESS_POLICY_DENIED,
-                olm.olmId
-            );
+            sendOlmError(OlmErrorCodes.ORG_ACCESS_POLICY_DENIED, olm.olmId);
             return;
         }
     }