diff --git a/server/routers/olm/handleOlmRegisterMessage.ts b/server/routers/olm/handleOlmRegisterMessage.ts
index a4a62973d..aaaf81c41 100644
--- a/server/routers/olm/handleOlmRegisterMessage.ts
+++ b/server/routers/olm/handleOlmRegisterMessage.ts
@@ -22,14 +22,14 @@ import { canCompress } from "@server/lib/clientVersionChecks";
 import config from "@server/lib/config";
 
 export const handleOlmRegisterMessage: MessageHandler = async (context) => {
-    logger.info("Handling register olm message!");
+    logger.info("[handleOlmRegisterMessage] Handling register olm message");
     const { message, client: c, sendToClient } = context;
     const olm = c as Olm;
 
     const now = Math.floor(Date.now() / 1000);
 
     if (!olm) {
-        logger.warn("Olm not found");
+        logger.warn("[handleOlmRegisterMessage] Olm not found");
         return;
     }
 
@@ -46,16 +46,19 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
     } = message.data;
 
     if (!olm.clientId) {
-        logger.warn("Olm client ID not found");
+        logger.warn("[handleOlmRegisterMessage] Olm client ID not found");
         sendOlmError(OlmErrorCodes.CLIENT_ID_NOT_FOUND, olm.olmId);
         return;
     }
 
-    logger.debug("Handling fingerprint insertion for olm register...", {
-        olmId: olm.olmId,
-        fingerprint,
-        postures
-    });
+    logger.debug(
+        "[handleOlmRegisterMessage] Handling fingerprint insertion for olm register...",
+        {
+            olmId: olm.olmId,
+            fingerprint,
+            postures
+        }
+    );
 
     const isUserDevice = olm.userId !== null && olm.userId !== undefined;
 
@@ -85,14 +88,17 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
         .limit(1);
 
     if (!client) {
-        logger.warn("Client ID not found");
+        logger.warn("[handleOlmRegisterMessage] Client not found", {
+            clientId: olm.clientId
+        });
         sendOlmError(OlmErrorCodes.CLIENT_NOT_FOUND, olm.olmId);
         return;
     }
 
     if (client.blocked) {
         logger.debug(
-            `Client ${client.clientId} is blocked. Ignoring register.`
+            `[handleOlmRegisterMessage] Client ${client.clientId} is blocked. Ignoring register.`,
+            { orgId: client.orgId }
         );
         sendOlmError(OlmErrorCodes.CLIENT_BLOCKED, olm.olmId);
         return;
@@ -100,7 +106,8 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
 
     if (client.approvalState == "pending") {
         logger.debug(
-            `Client ${client.clientId} approval is pending. Ignoring register.`
+            `[handleOlmRegisterMessage] Client ${client.clientId} approval is pending. Ignoring register.`,
+            { orgId: client.orgId }
         );
         sendOlmError(OlmErrorCodes.CLIENT_PENDING, olm.olmId);
         return;
@@ -128,14 +135,18 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
         .limit(1);
 
     if (!org) {
-        logger.warn("Org not found");
+        logger.warn("[handleOlmRegisterMessage] Org not found", {
+            orgId: client.orgId
+        });
         sendOlmError(OlmErrorCodes.ORG_NOT_FOUND, olm.olmId);
         return;
     }
 
     if (orgId) {
         if (!olm.userId) {
-            logger.warn("Olm has no user ID");
+            logger.warn("[handleOlmRegisterMessage] Olm has no user ID", {
+                orgId: client.orgId
+            });
             sendOlmError(OlmErrorCodes.USER_ID_NOT_FOUND, olm.olmId);
             return;
         }
@@ -143,12 +154,18 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
         const { session: userSession, user } =
             await validateSessionToken(userToken);
         if (!userSession || !user) {
-            logger.warn("Invalid user session for olm register");
+            logger.warn(
+                "[handleOlmRegisterMessage] Invalid user session for olm register",
+                { orgId: client.orgId }
+            );
             sendOlmError(OlmErrorCodes.INVALID_USER_SESSION, olm.olmId);
             return;
         }
         if (user.userId !== olm.userId) {
-            logger.warn("User ID mismatch for olm register");
+            logger.warn(
+                "[handleOlmRegisterMessage] User ID mismatch for olm register",
+                { orgId: client.orgId }
+            );
             sendOlmError(OlmErrorCodes.USER_ID_MISMATCH, olm.olmId);
             return;
         }
@@ -163,11 +180,15 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
             sessionId // this is the user token passed in the message
         });
 
-        logger.debug("Policy check result:", policyCheck);
+        logger.debug("[handleOlmRegisterMessage] Policy check result", {
+            orgId: client.orgId,
+            policyCheck
+        });
 
         if (policyCheck?.error) {
             logger.error(
-                `Error checking access policies for olm user ${olm.userId} in org ${orgId}: ${policyCheck?.error}`
+                `[handleOlmRegisterMessage] Error checking access policies for olm user ${olm.userId} in org ${orgId}: ${policyCheck?.error}`,
+                { orgId: client.orgId }
             );
             sendOlmError(OlmErrorCodes.ORG_ACCESS_POLICY_DENIED, olm.olmId);
             return;
@@ -175,7 +196,8 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
 
         if (policyCheck.policies?.passwordAge?.compliant === false) {
             logger.warn(
-                `Olm user ${olm.userId} has non-compliant password age for org ${orgId}`
+                `[handleOlmRegisterMessage] Olm user ${olm.userId} has non-compliant password age for org ${orgId}`,
+                { orgId: client.orgId }
             );
             sendOlmError(
                 OlmErrorCodes.ORG_ACCESS_POLICY_PASSWORD_EXPIRED,
@@ -186,7 +208,8 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
             policyCheck.policies?.maxSessionLength?.compliant === false
         ) {
             logger.warn(
-                `Olm user ${olm.userId} has non-compliant session length for org ${orgId}`
+                `[handleOlmRegisterMessage] Olm user ${olm.userId} has non-compliant session length for org ${orgId}`,
+                { orgId: client.orgId }
             );
             sendOlmError(
                 OlmErrorCodes.ORG_ACCESS_POLICY_SESSION_EXPIRED,
@@ -195,7 +218,8 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
             return;
         } else if (policyCheck.policies?.requiredTwoFactor === false) {
             logger.warn(
-                `Olm user ${olm.userId} does not have 2FA enabled for org ${orgId}`
+                `[handleOlmRegisterMessage] Olm user ${olm.userId} does not have 2FA enabled for org ${orgId}`,
+                { orgId: client.orgId }
             );
             sendOlmError(
                 OlmErrorCodes.ORG_ACCESS_POLICY_2FA_REQUIRED,
@@ -204,7 +228,8 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
             return;
         } else if (!policyCheck.allowed) {
             logger.warn(
-                `Olm user ${olm.userId} does not pass access policies for org ${orgId}: ${policyCheck.error}`
+                `[handleOlmRegisterMessage] Olm user ${olm.userId} does not pass access policies for org ${orgId}: ${policyCheck.error}`,
+                { orgId: client.orgId }
             );
             sendOlmError(OlmErrorCodes.ORG_ACCESS_POLICY_DENIED, olm.olmId);
             return;
@@ -226,29 +251,39 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
         sitesCountResult.length > 0 ? sitesCountResult[0].count : 0;
 
     // Prepare an array to store site configurations
-    logger.debug(`Found ${sitesCount} sites for client ${client.clientId}`);
+    logger.debug(
+        `[handleOlmRegisterMessage] Found ${sitesCount} sites for client ${client.clientId}`,
+        { orgId: client.orgId }
+    );
 
     let jitMode = false;
     if (sitesCount > 250 && build == "saas") {
         // THIS IS THE MAX ON THE BUSINESS TIER
         // we have too many sites
         // If we have too many sites we need to drop into fully JIT mode by not sending any of the sites
-        logger.info("Too many sites (%d), dropping into JIT mode", sitesCount);
+        logger.info(
+            `[handleOlmRegisterMessage] Too many sites (${sitesCount}), dropping into JIT mode`,
+            { orgId: client.orgId }
+        );
         jitMode = true;
     }
 
     logger.debug(
-        `Olm client ID: ${client.clientId}, Public Key: ${publicKey}, Relay: ${relay}`
+        `[handleOlmRegisterMessage] Olm client ID: ${client.clientId}, Public Key: ${publicKey}, Relay: ${relay}`,
+        { orgId: client.orgId }
     );
 
     if (!publicKey) {
-        logger.warn("Public key not provided");
+        logger.warn("[handleOlmRegisterMessage] Public key not provided", {
+            orgId: client.orgId
+        });
         return;
     }
 
     if (client.pubKey !== publicKey || client.archived) {
         logger.info(
-            "Public key mismatch. Updating public key and clearing session info..."
+            "[handleOlmRegisterMessage] Public key mismatch. Updating public key and clearing session info...",
+            { orgId: client.orgId }
         );
         // Update the client's public key
         await db
@@ -274,12 +309,13 @@ export const handleOlmRegisterMessage: MessageHandler = async (context) => {
     // TODO: I still think there is a better way to do this rather than locking it out here but ???
     if (now - (client.lastHolePunch || 0) > 5 && sitesCount > 0) {
         logger.warn(
-            `Client last hole punch is too old and we have sites to send; skipping this register. The client is failing to hole punch and identify its network address with the server. Can the client reach the server on UDP port ${config.getRawConfig().gerbil.clients_start_port}?`
+            `[handleOlmRegisterMessage] Client last hole punch is too old and we have sites to send; skipping this register. The client is failing to hole punch and identify its network address with the server. Can the client reach the server on UDP port ${config.getRawConfig().gerbil.clients_start_port}?`,
+            { orgId: client.orgId }
         );
         return;
     }
 
-   // NOTE: its important that the client here is the old client and the public key is the new key
+    // NOTE: its important that the client here is the old client and the public key is the new key
     const siteConfigurations = await buildSiteConfigurationForOlmClient(
         client,
         publicKey,