diff --git a/packages/cli-repl/README.md b/packages/cli-repl/README.md
index 8900f5ff7e..6c6ceb22ef 100644
--- a/packages/cli-repl/README.md
+++ b/packages/cli-repl/README.md
@@ -99,25 +99,24 @@ bus.emit('mongosh:connect', {
 })
 ```
 
-### bus.on('mongosh:new-user', telemetryAnonymousId, enableTelemetry)
-Where `telemetryAnonymousId` is a [BSON ObjectID][object-id] and `enableTelemetry` is a boolean flag.
-This is used for telemetry tracking when the user initially uses mongosh.
+### bus.on('mongosh:new-user', telemetryUserIdentity, enableTelemetry)
+Where `telemetryUserIdentity` is `userId` and `anonymousId` which are both a [BSON ObjectID][object-id].
+And `enableTelemetry` is a boolean flag.
+This is used internally to update telemetry preferences.
 
 Example:
 ```js
-bus.emit('mongosh:new-user', '12394dfjvnaw3uw3erdf', true)
+bus.emit('mongosh:new-user', { userId: '12394dfjvnaw3uw3erdf', anonymousId: '12394dfjvnaw3uw3erdf' }, true)
 ```
 
 ### bus.on('mongosh:update-user', telemetryUserIdentity, enableTelemetry)
-Initially, we used `userId` as Segment user identifier, but this usage is being deprecated.
-The `anonymousId` should be used instead. We keep sending `userId` to Segment for old users though to preserve their analytics.
-Where `userID`/`anonymousId` is a [BSON ObjectID][object-id] and `enableTelemetry` is a boolean flag.
-This is used internally to update telemetry preferences and `userID`/`anonymousId` in the
-logger.
+Where `telemetryUserIdentity` is `userId` and `anonymousId` which are both a [BSON ObjectID][object-id].
+And `enableTelemetry` is a boolean flag.
+This is used internally to update telemetry preferences.
 
 Example:
 ```js
-bus.emit('mongosh:update-user', { userId: undefined, anonymousId: '12394dfjvnaw3uw3erdf' } , false)
+bus.emit('mongosh:update-user', { userId: '12394dfjvnaw3uw3erdf', anonymousId: null } , false)
 ```
 
 ### bus.on('mongosh:error', error)
diff --git a/packages/cli-repl/src/cli-repl.spec.ts b/packages/cli-repl/src/cli-repl.spec.ts
index 48967f43c9..a745b2c30b 100644
--- a/packages/cli-repl/src/cli-repl.spec.ts
+++ b/packages/cli-repl/src/cli-repl.spec.ts
@@ -113,7 +113,7 @@ describe('CliRepl', () => {
       it('does not store config options on disk that have not been changed', async() => {
         let content = await fs.readFile(path.join(tmpdir.path, 'config'), { encoding: 'utf8' });
         expect(Object.keys(EJSON.parse(content))).to.deep.equal([
-          'telemetryAnonymousId', 'enableTelemetry', 'disableGreetingMessage'
+          'userId', 'telemetryAnonymousId', 'enableTelemetry', 'disableGreetingMessage'
         ]);
 
         input.write('config.set("inspectDepth", config.get("inspectDepth"))\n');
@@ -121,7 +121,7 @@ describe('CliRepl', () => {
         await waitEval(cliRepl.bus);
         content = await fs.readFile(path.join(tmpdir.path, 'config'), { encoding: 'utf8' });
         expect(Object.keys(EJSON.parse(content))).to.deep.equal([
-          'telemetryAnonymousId', 'enableTelemetry', 'disableGreetingMessage', 'inspectDepth'
+          'userId', 'telemetryAnonymousId', 'enableTelemetry', 'disableGreetingMessage', 'inspectDepth'
         ]);
 
         // When a new REPL is created:
@@ -129,7 +129,7 @@ describe('CliRepl', () => {
         await cliRepl.start('', {});
         content = await fs.readFile(path.join(tmpdir.path, 'config'), { encoding: 'utf8' });
         expect(Object.keys(EJSON.parse(content))).to.deep.equal([
-          'telemetryAnonymousId', 'enableTelemetry', 'disableGreetingMessage', 'inspectDepth'
+          'userId', 'telemetryAnonymousId', 'enableTelemetry', 'disableGreetingMessage', 'inspectDepth'
         ]);
       });
 
@@ -286,16 +286,16 @@ describe('CliRepl', () => {
     });
 
     context('during startup', () => {
-      it('persists telemetryAnonymousId', async() => {
-        const telemetryAnonymousIds: string[] = [];
+      it('persists userId and telemetryAnonymousId', async() => {
+        const telemetryUserIdentitys: { userId?: string; anonymousId?: string }[] = [];
         for (let i = 0; i < 2; i++) {
           cliRepl = new CliRepl(cliReplOptions);
-          cliRepl.bus.on('mongosh:new-user', telemetryAnonymousId => telemetryAnonymousIds.push(telemetryAnonymousId));
-          cliRepl.bus.on('mongosh:update-user', telemetryUserIdentity => telemetryAnonymousIds.push(telemetryUserIdentity.anonymousId));
+          cliRepl.bus.on('mongosh:new-user', telemetryUserIdentity => telemetryUserIdentitys.push(telemetryUserIdentity));
+          cliRepl.bus.on('mongosh:update-user', telemetryUserIdentity => telemetryUserIdentitys.push(telemetryUserIdentity));
           await cliRepl.start('', {});
         }
-        expect(telemetryAnonymousIds).to.have.lengthOf(2);
-        expect([...new Set(telemetryAnonymousIds)]).to.have.lengthOf(1);
+        expect(telemetryUserIdentitys).to.have.lengthOf(2);
+        expect(telemetryUserIdentitys[0]).to.deep.equal(telemetryUserIdentitys[1])
       });
 
       it('emits error for invalid config', async() => {
diff --git a/packages/cli-repl/src/cli-repl.ts b/packages/cli-repl/src/cli-repl.ts
index ad8f337623..684b3fe5fa 100644
--- a/packages/cli-repl/src/cli-repl.ts
+++ b/packages/cli-repl/src/cli-repl.ts
@@ -66,7 +66,7 @@ export type CliReplOptions = {
 } & Pick<MongoshNodeReplOptions, 'nodeReplOptions'>;
 
 /** The set of config options that is *always* available in config files stored on the file system. */
-type CliUserConfigOnDisk = Partial<CliUserConfig> & Pick<CliUserConfig, 'enableTelemetry' | 'telemetryAnonymousId'>;
+type CliUserConfigOnDisk = Partial<CliUserConfig> & Pick<CliUserConfig, 'enableTelemetry' | 'userId' | 'telemetryAnonymousId'>;
 
 /**
  * The REPL used from the terminal.
@@ -104,8 +104,11 @@ class CliRepl implements MongoshIOProvider {
     this.output = options.output;
     this.analyticsOptions = options.analyticsOptions;
     this.onExit = options.onExit;
+
+    const id = new bson.ObjectId().toString();
     this.config = {
-      telemetryAnonymousId: new bson.ObjectId().toString(),
+      userId: id,
+      telemetryAnonymousId: id,
       enableTelemetry: true
     };
 
@@ -118,11 +121,11 @@ class CliRepl implements MongoshIOProvider {
       })
       .on('new-config', (config: CliUserConfigOnDisk) => {
         this.setTelemetryEnabled(config.enableTelemetry);
-        this.bus.emit('mongosh:new-user', config.telemetryAnonymousId);
+        this.bus.emit('mongosh:new-user', { userId: config.userId, anonymousId: config.telemetryAnonymousId });
       })
       .on('update-config', (config: CliUserConfigOnDisk) => {
         this.setTelemetryEnabled(config.enableTelemetry);
-        this.bus.emit('mongosh:update-user', { userId: config.userId, anonymousId: config.telemetryAnonymousId ?? config.userId });
+        this.bus.emit('mongosh:update-user', { userId: config.userId, anonymousId: config.telemetryAnonymousId });
       });
 
     this.mongocryptdManager = new MongocryptdManager(
diff --git a/packages/cli-repl/test/e2e.spec.ts b/packages/cli-repl/test/e2e.spec.ts
index 04a147738d..5ce3df71b6 100644
--- a/packages/cli-repl/test/e2e.spec.ts
+++ b/packages/cli-repl/test/e2e.spec.ts
@@ -884,6 +884,7 @@ describe('e2e', function() {
       describe('config file', () => {
         it('sets up a config file', async() => {
           const config = await readConfig();
+          expect(config.userId).to.match(/^[a-f0-9]{24}$/);
           expect(config.telemetryAnonymousId).to.match(/^[a-f0-9]{24}$/);
           expect(config.enableTelemetry).to.be.true;
           expect(config.disableGreetingMessage).to.be.true;
diff --git a/packages/logging/src/analytics-helpers.spec.ts b/packages/logging/src/analytics-helpers.spec.ts
index f26ebb8fca..864d3e9e17 100644
--- a/packages/logging/src/analytics-helpers.spec.ts
+++ b/packages/logging/src/analytics-helpers.spec.ts
@@ -17,18 +17,18 @@ describe('ToggleableAnalytics', () => {
     const toggleable = new ToggleableAnalytics(target);
     expect(events).to.have.lengthOf(0);
 
-    toggleable.identify({ anonymousId: 'me', traits: { platform: '1234' } });
-    toggleable.track({ anonymousId: 'me', event: 'something', properties: { mongosh_version: '1.2.3' } });
+    toggleable.identify({ userId: 'me', traits: { platform: '1234' } });
+    toggleable.track({ userId: 'me', event: 'something', properties: { mongosh_version: '1.2.3' } });
     expect(events).to.have.lengthOf(0);
 
     toggleable.enable();
     expect(events).to.have.lengthOf(2);
 
-    toggleable.track({ anonymousId: 'me', event: 'something2', properties: { mongosh_version: '1.2.3' } });
+    toggleable.track({ userId: 'me', event: 'something2', properties: { mongosh_version: '1.2.3' } });
     expect(events).to.have.lengthOf(3);
 
     toggleable.pause();
-    toggleable.track({ anonymousId: 'me', event: 'something3', properties: { mongosh_version: '1.2.3' } });
+    toggleable.track({ userId: 'me', event: 'something3', properties: { mongosh_version: '1.2.3' } });
     expect(events).to.have.lengthOf(3);
 
     toggleable.disable();
@@ -36,9 +36,9 @@ describe('ToggleableAnalytics', () => {
     toggleable.enable();
 
     expect(events).to.deep.equal([
-      [ 'identify', { anonymousId: 'me', traits: { platform: '1234' } } ],
-      [ 'track', { anonymousId: 'me', event: 'something', properties: { mongosh_version: '1.2.3' } } ],
-      [ 'track', { anonymousId: 'me', event: 'something2', properties: { mongosh_version: '1.2.3' } } ]
+      [ 'identify', { userId: 'me', traits: { platform: '1234' } } ],
+      [ 'track', { userId: 'me', event: 'something', properties: { mongosh_version: '1.2.3' } } ],
+      [ 'track', { userId: 'me', event: 'something2', properties: { mongosh_version: '1.2.3' } } ]
     ]);
   });
 });
diff --git a/packages/logging/src/analytics-helpers.ts b/packages/logging/src/analytics-helpers.ts
index 3d7b5ae1a3..a4bd3c7d50 100644
--- a/packages/logging/src/analytics-helpers.ts
+++ b/packages/logging/src/analytics-helpers.ts
@@ -1,16 +1,18 @@
+export type MongoshAnalyticsIdentity = {
+  userId: string;
+} | {
+  anonymousId: string;
+}
+
 /**
  * General interface for an Analytics provider that mongosh can use.
  */
 export interface MongoshAnalytics {
-  identify(message: {
-    userId?: string,
-    anonymousId: string,
+  identify(message: MongoshAnalyticsIdentity & {
     traits: { platform: string }
   }): void;
 
-  track(message: {
-    userId?: string,
-    anonymousId: string,
+  track(message: MongoshAnalyticsIdentity & {
     event: string,
     properties: {
       // eslint-disable-next-line camelcase
diff --git a/packages/logging/src/setup-logger-and-telemetry.spec.ts b/packages/logging/src/setup-logger-and-telemetry.spec.ts
index 56c1caa129..c0806eeb0a 100644
--- a/packages/logging/src/setup-logger-and-telemetry.spec.ts
+++ b/packages/logging/src/setup-logger-and-telemetry.spec.ts
@@ -10,7 +10,7 @@ describe('setupLoggerAndTelemetry', () => {
   let analyticsOutput: ['identify'|'track'|'log', any][];
   let bus: MongoshBus;
 
-  const telemetryAnonymousId = '53defe995fa47e6c13102d9d';
+  const userId = '53defe995fa47e6c13102d9d';
   const logId = '5fb3c20ee1507e894e5340f3';
 
   const logger = new MongoLogWriter(logId, `/tmp/${logId}_log`, {
@@ -36,8 +36,8 @@ describe('setupLoggerAndTelemetry', () => {
     expect(logOutput).to.have.lengthOf(0);
     expect(analyticsOutput).to.be.empty;
 
-    bus.emit('mongosh:new-user', telemetryAnonymousId);
-    bus.emit('mongosh:update-user', { anonymousId: telemetryAnonymousId });
+    bus.emit('mongosh:new-user', { userId, anonymousId: userId });
+    bus.emit('mongosh:update-user', { userId, anonymousId: userId });
     bus.emit('mongosh:connect', {
       uri: 'mongodb://localhost/',
       is_localhost: true,
@@ -364,7 +364,7 @@ describe('setupLoggerAndTelemetry', () => {
     expect(logOutput).to.have.lengthOf(0);
     expect(analyticsOutput).to.be.empty;
 
-    bus.emit('mongosh:new-user', telemetryAnonymousId);
+    bus.emit('mongosh:new-user', { userId, anonymousId: userId });
 
     logOutput = [];
     analyticsOutput = [];
@@ -454,7 +454,7 @@ describe('setupLoggerAndTelemetry', () => {
       ],
     ]);
 
-    bus.emit('mongosh:new-user', telemetryAnonymousId);
+    bus.emit('mongosh:new-user', { userId, anonymousId: userId });
     logOutput = [];
     analyticsOutput = [];
 
diff --git a/packages/logging/src/setup-logger-and-telemetry.ts b/packages/logging/src/setup-logger-and-telemetry.ts
index afb9586855..881d3b0dc6 100644
--- a/packages/logging/src/setup-logger-and-telemetry.ts
+++ b/packages/logging/src/setup-logger-and-telemetry.ts
@@ -29,8 +29,7 @@ import type {
   SnippetsTransformErrorEvent,
   EditorRunEditCommandEvent,
   EditorReadVscodeExtensionsDoneEvent,
-  EditorReadVscodeExtensionsFailedEvent,
-  TelemetryUserIdentity
+  EditorReadVscodeExtensionsFailedEvent
 } from '@mongosh/types';
 import { inspect } from 'util';
 import { MongoLogWriter, mongoLogId } from 'mongodb-log-writer';
@@ -73,7 +72,18 @@ export function setupLoggerAndTelemetry(
   userTraits: any,
   mongosh_version: string): void {
   const { logId } = log;
-  let telemetryUserIdentity: TelemetryUserIdentity;
+  let userId: string;
+  let telemetryAnonymousId: string;
+
+  const getTelemetryUserIdentity = () => {
+    if (telemetryAnonymousId) {
+      return {
+        anonymousId: telemetryAnonymousId
+      };
+    }
+
+    return { userId };
+  };
 
   // We emit different analytics events for loading files and evaluating scripts
   // depending on whether we're already in the REPL or not yet. We store the
@@ -96,15 +106,15 @@ export function setupLoggerAndTelemetry(
     const { uri: _uri, ...argsWithoutUri } = args; // eslint-disable-line @typescript-eslint/no-unused-vars
     const params = {
       session_id: logId,
-      userId: telemetryUserIdentity?.userId,
-      telemetryAnonymousId: telemetryUserIdentity?.anonymousId,
+      userId,
+      telemetryAnonymousId,
       connectionUri,
       ...argsWithoutUri
     };
     log.info('MONGOSH', mongoLogId(1_000_000_004), 'connect', 'Connecting to server', params);
 
     analytics.track({
-      ...telemetryUserIdentity,
+      ...getTelemetryUserIdentity(),
       event: 'New Connection',
       properties: {
         mongosh_version,
@@ -114,24 +124,31 @@ export function setupLoggerAndTelemetry(
     });
   });
 
-  bus.on('mongosh:new-user', function(anonymousId: string) {
-    telemetryUserIdentity = { anonymousId };
-    analytics.identify({ anonymousId, traits: userTraits });
-  });
-
-  bus.on('mongosh:update-user', function(updatedTelemetryUserIdentity: TelemetryUserIdentity) {
-    telemetryUserIdentity = updatedTelemetryUserIdentity;
-
-    const telemetryIdentifyArg: TelemetryUserIdentity & { traits: any } = {
-      anonymousId: telemetryUserIdentity.anonymousId,
+  bus.on('mongosh:new-user', function(newTelemetryUserIdentity: { userId: string; anonymousId: string }) {
+    if (!newTelemetryUserIdentity.anonymousId) {
+      userId = newTelemetryUserIdentity.userId;
+    }
+    telemetryAnonymousId = newTelemetryUserIdentity.anonymousId;
+    analytics.identify({
+      anonymousId: newTelemetryUserIdentity.anonymousId,
       traits: userTraits
-    };
+    });
+  });
 
-    if (telemetryUserIdentity?.userId) {
-      telemetryIdentifyArg.userId = telemetryUserIdentity.userId;
+  bus.on('mongosh:update-user', function(updatedTelemetryUserIdentity: { userId: string; anonymousId?: string }) {
+    if (updatedTelemetryUserIdentity.anonymousId) {
+      telemetryAnonymousId = updatedTelemetryUserIdentity.anonymousId;
+      analytics.identify({
+        anonymousId: updatedTelemetryUserIdentity.anonymousId,
+        traits: userTraits
+      });
+    } else {
+      userId = updatedTelemetryUserIdentity.userId;
+      analytics.identify({
+        userId: updatedTelemetryUserIdentity.userId,
+        traits: userTraits
+      });
     }
-
-    analytics.identify(telemetryIdentifyArg);
     log.info('MONGOSH', mongoLogId(1_000_000_005), 'config', 'User updated');
   });
 
@@ -144,7 +161,7 @@ export function setupLoggerAndTelemetry(
 
     if (error.name.includes('Mongosh')) {
       analytics.track({
-        ...telemetryUserIdentity,
+        ...getTelemetryUserIdentity(),
         event: 'Error',
         properties: {
           mongosh_version,
@@ -169,7 +186,7 @@ export function setupLoggerAndTelemetry(
     log.info('MONGOSH', mongoLogId(1_000_000_008), 'shell-api', 'Used "use" command', args);
 
     analytics.track({
-      ...telemetryUserIdentity,
+      ...getTelemetryUserIdentity(),
       event: 'Use',
       properties: {
         mongosh_version
@@ -181,7 +198,7 @@ export function setupLoggerAndTelemetry(
     log.info('MONGOSH', mongoLogId(1_000_000_009), 'shell-api', 'Used "show" command', args);
 
     analytics.track({
-      ...telemetryUserIdentity,
+      ...getTelemetryUserIdentity(),
       event: 'Show',
       properties: {
         mongosh_version,
@@ -209,7 +226,7 @@ export function setupLoggerAndTelemetry(
     log.info('MONGOSH', mongoLogId(1_000_000_012), 'shell-api', 'Loading file via load()', args);
 
     analytics.track({
-      ...telemetryUserIdentity,
+      ...getTelemetryUserIdentity(),
       event: hasStartedMongoshRepl ? 'Script Loaded' : 'Script Loaded CLI',
       properties: {
         mongosh_version,
@@ -223,7 +240,7 @@ export function setupLoggerAndTelemetry(
     log.info('MONGOSH', mongoLogId(1_000_000_013), 'repl', 'Evaluating script passed on the command line');
 
     analytics.track({
-      ...telemetryUserIdentity,
+      ...getTelemetryUserIdentity(),
       event: 'Script Evaluated',
       properties: {
         mongosh_version,
@@ -236,7 +253,7 @@ export function setupLoggerAndTelemetry(
     log.info('MONGOSH', mongoLogId(1_000_000_014), 'repl', 'Loading .mongoshrc.js');
 
     analytics.track({
-      ...telemetryUserIdentity,
+      ...getTelemetryUserIdentity(),
       event: 'Mongoshrc Loaded',
       properties: {
         mongosh_version
@@ -248,7 +265,7 @@ export function setupLoggerAndTelemetry(
     log.info('MONGOSH', mongoLogId(1_000_000_015), 'repl', 'Warning about .mongorc.js/.mongoshrc.js mismatch');
 
     analytics.track({
-      ...telemetryUserIdentity,
+      ...getTelemetryUserIdentity(),
       event: 'Mongorc Warning',
       properties: {
         mongosh_version
@@ -324,7 +341,7 @@ export function setupLoggerAndTelemetry(
 
     if (ev.args[0] === 'install') {
       analytics.track({
-        ...telemetryUserIdentity,
+        ...getTelemetryUserIdentity(),
         event: 'Snippet Install',
         properties: {
           mongosh_version
@@ -360,7 +377,7 @@ export function setupLoggerAndTelemetry(
       log.warn('MONGOSH', mongoLogId(1_000_000_033), 'shell-api', 'Deprecated API call', entry);
 
       analytics.track({
-        ...telemetryUserIdentity,
+        ...getTelemetryUserIdentity(),
         event: 'Deprecated Method',
         properties: {
           mongosh_version,
@@ -370,7 +387,7 @@ export function setupLoggerAndTelemetry(
     }
     for (const [entry, count] of apiCalls) {
       analytics.track({
-        ...telemetryUserIdentity,
+        ...getTelemetryUserIdentity(),
         event: 'API Call',
         properties: {
           mongosh_version,
diff --git a/packages/types/src/index.ts b/packages/types/src/index.ts
index 0eef4f9b5e..81ea094c7c 100644
--- a/packages/types/src/index.ts
+++ b/packages/types/src/index.ts
@@ -167,11 +167,6 @@ export interface EditorReadVscodeExtensionsFailedEvent {
   error: Error;
 }
 
-export interface TelemetryUserIdentity {
-  userId?: string;
-  anonymousId: string;
-}
-
 export interface MongoshBusEventsMap extends ConnectEventMap {
   /**
    * Signals a connection to a MongoDB instance has been established
@@ -181,11 +176,11 @@ export interface MongoshBusEventsMap extends ConnectEventMap {
   /**
    * Signals that the shell is started by a new user.
    */
-  'mongosh:new-user': (id: string) => void;
+  'mongosh:new-user': (identity: { userId: string; anonymousId: string }) => void;
   /**
    * Signals a change of the user telemetry settings.
    */
-  'mongosh:update-user': (identity: TelemetryUserIdentity) => void;
+  'mongosh:update-user': (identity: { userId: string; anonymousId?: string }) => void;
   /**
    * Signals an error that should be logged or potentially tracked by analytics.
    */
@@ -417,7 +412,7 @@ export class SnippetShellUserConfigValidator extends ShellUserConfigValidator {
 }
 
 export class CliUserConfig extends SnippetShellUserConfig {
-  userId?: string;
+  userId = '';
   telemetryAnonymousId = '';
   disableGreetingMessage = false;
   forceDisableTelemetry = false;