diff --git a/server/endpoints/chat.js b/server/endpoints/chat.js
index de2a4b45..b0afed76 100644
--- a/server/endpoints/chat.js
+++ b/server/endpoints/chat.js
@@ -64,11 +64,15 @@ function chatEndpoints(app) {
         }
 
         const result = await chatWithWorkspace(workspace, message, mode, user);
-        await Telemetry.sendTelemetry("sent_chat", {
-          multiUserMode: multiUserMode(response),
-          LLMSelection: process.env.LLM_PROVIDER || "openai",
-          VectorDbSelection: process.env.VECTOR_DB || "pinecone",
-        });
+        await Telemetry.sendTelemetry(
+          "sent_chat",
+          {
+            multiUserMode: multiUserMode(response),
+            LLMSelection: process.env.LLM_PROVIDER || "openai",
+            VectorDbSelection: process.env.VECTOR_DB || "pinecone",
+          },
+          user?.id
+        );
         response.status(200).json({ ...result });
       } catch (e) {
         console.error(e);
diff --git a/server/endpoints/system.js b/server/endpoints/system.js
index 202ba376..b6868ec1 100644
--- a/server/endpoints/system.js
+++ b/server/endpoints/system.js
@@ -134,6 +134,11 @@ function systemEndpoints(app) {
           return;
         }
 
+        await Telemetry.sendTelemetry(
+          "login_event",
+          { multiUserMode: false },
+          existingUser?.id
+        );
         response.status(200).json({
           valid: true,
           user: existingUser,
@@ -155,6 +160,7 @@ function systemEndpoints(app) {
           return;
         }
 
+        await Telemetry.sendTelemetry("login_event", { multiUserMode: false });
         response.status(200).json({
           valid: true,
           token: makeJWT({ p: password }, "30d"),
@@ -325,7 +331,9 @@ function systemEndpoints(app) {
           true
         );
         if (process.env.NODE_ENV === "production") await dumpENV();
-        await Telemetry.sendTelemetry("enabled_multi_user_mode");
+        await Telemetry.sendTelemetry("enabled_multi_user_mode", {
+          multiUserMode: true,
+        });
         response.status(200).json({ success: !!user, error });
       } catch (e) {
         await User.delete({});
diff --git a/server/endpoints/workspaces.js b/server/endpoints/workspaces.js
index 51ffc23e..c32eb475 100644
--- a/server/endpoints/workspaces.js
+++ b/server/endpoints/workspaces.js
@@ -23,11 +23,15 @@ function workspaceEndpoints(app) {
       const user = await userFromSession(request, response);
       const { name = null, onboardingComplete = false } = reqBody(request);
       const { workspace, message } = await Workspace.new(name, user?.id);
-      await Telemetry.sendTelemetry("workspace_created", {
-        multiUserMode: multiUserMode(response),
-        LLMSelection: process.env.LLM_PROVIDER || "openai",
-        VectorDbSelection: process.env.VECTOR_DB || "pinecone",
-      });
+      await Telemetry.sendTelemetry(
+        "workspace_created",
+        {
+          multiUserMode: multiUserMode(response),
+          LLMSelection: process.env.LLM_PROVIDER || "openai",
+          VectorDbSelection: process.env.VECTOR_DB || "pinecone",
+        },
+        user?.id
+      );
       if (onboardingComplete === true)
         await Telemetry.sendTelemetry("onboarding_complete");
 
diff --git a/server/models/telemetry.js b/server/models/telemetry.js
index 19c47f7a..d1f0b038 100644
--- a/server/models/telemetry.js
+++ b/server/models/telemetry.js
@@ -28,12 +28,14 @@ const Telemetry = {
     return new PostHog(this.pubkey);
   },
 
-  sendTelemetry: async function (event, properties = {}) {
+  sendTelemetry: async function (event, properties = {}, subUserId = null) {
     try {
-      const { client, distinctId } = await this.connect();
+      const { client, distinctId: systemId } = await this.connect();
       if (!client) return;
+      const distinctId = !!subUserId ? `${systemId}::${subUserId}` : systemId;
       console.log(`\x1b[32m[TELEMETRY SENT]\x1b[0m`, {
         event,
+        distinctId,
         properties,
       });
       client.capture({