diff --git a/docs/telemetry-events.md b/docs/telemetry-events.md
index 141c7a60ef007..8e2d30d1b2c3e 100644
--- a/docs/telemetry-events.md
+++ b/docs/telemetry-events.md
@@ -521,6 +521,19 @@ or
 }
 ```
 
+### cloudIntegrations/refreshConnection/skippedUnusualToken
+
+> Sent when a connection session has a missing expiry date
+or when connection refresh is skipped due to being a non-cloud session
+
+```typescript
+{
+  'cloud': boolean,
+  'integration.id': string,
+  'reason': 'skip-non-cloud' | 'missing-expiry'
+}
+```
+
 ### cloudIntegrations/settingsOpened
 
 > Sent when a user chooses to manage the cloud integrations
diff --git a/src/constants.telemetry.ts b/src/constants.telemetry.ts
index a904344175177..c757c862b7b45 100644
--- a/src/constants.telemetry.ts
+++ b/src/constants.telemetry.ts
@@ -84,6 +84,10 @@ export interface TelemetryEvents extends WebviewShowAbortedEvents, WebviewShownE
 	/** Sent when refreshing a provider token from the api fails */
 	'cloudIntegrations/refreshConnection/failed': CloudIntegrationsRefreshConnectionFailedEvent;
 
+	/** Sent when a connection session has a missing expiry date
+	 * or when connection refresh is skipped due to being a non-cloud session */
+	'cloudIntegrations/refreshConnection/skippedUnusualToken': CloudIntegrationsRefreshConnectionSkipUnusualTokenEvent;
+
 	/** Sent when a cloud-based hosting provider is connected */
 	'cloudIntegrations/hosting/connected': CloudIntegrationsHostingConnectedEvent;
 	/** Sent when a cloud-based hosting provider is disconnected */
@@ -407,6 +411,12 @@ interface CloudIntegrationsRefreshConnectionFailedEvent {
 	'integration.id': string | undefined;
 }
 
+interface CloudIntegrationsRefreshConnectionSkipUnusualTokenEvent {
+	'integration.id': string;
+	reason: 'skip-non-cloud' | 'missing-expiry';
+	cloud: boolean | undefined;
+}
+
 interface CloudIntegrationsHostingConnectedEvent {
 	'hostingProvider.provider': IntegrationId;
 	'hostingProvider.key': string;
diff --git a/src/plus/integrations/integration.ts b/src/plus/integrations/integration.ts
index 07ce8432cf533..c6b58bb5c202a 100644
--- a/src/plus/integrations/integration.ts
+++ b/src/plus/integrations/integration.ts
@@ -280,9 +280,20 @@ export abstract class IntegrationBase<
 		await this.container.storage.deleteWorkspace(this.connectedKey);
 	}
 
+	private skippedNonCloudReported = false;
 	@log()
 	async syncCloudConnection(state: 'connected' | 'disconnected', forceSync: boolean): Promise<void> {
-		if (this._session?.cloud === false) return;
+		if (this._session?.cloud === false) {
+			if (this.id !== HostingIntegrationId.GitHub && !this.skippedNonCloudReported) {
+				this.container.telemetry.sendEvent('cloudIntegrations/refreshConnection/skippedUnusualToken', {
+					'integration.id': this.id,
+					reason: 'skip-non-cloud',
+					cloud: false,
+				});
+				this.skippedNonCloudReported = true;
+			}
+			return;
+		}
 
 		switch (state) {
 			case 'connected':
@@ -327,6 +338,7 @@ export abstract class IntegrationBase<
 		return defaultValue;
 	}
 
+	private missingExpirityReported = false;
 	@gate()
 	protected async refreshSessionIfExpired(scope?: LogScope): Promise<void> {
 		if (this._session?.expiresAt != null && this._session.expiresAt < new Date()) {
@@ -336,6 +348,17 @@ export abstract class IntegrationBase<
 			} catch (ex) {
 				Logger.error(ex, scope);
 			}
+		} else if (
+			this._session?.expiresAt == null &&
+			this.id !== HostingIntegrationId.GitHub &&
+			!this.missingExpirityReported
+		) {
+			this.container.telemetry.sendEvent('cloudIntegrations/refreshConnection/skippedUnusualToken', {
+				'integration.id': this.id,
+				reason: 'missing-expiry',
+				cloud: this._session?.cloud,
+			});
+			this.missingExpirityReported = true;
 		}
 	}