diff --git a/app/durableObjects/ChatRoom.server.ts b/app/durableObjects/ChatRoom.server.ts
index b1e1fa42..9fa42472 100644
--- a/app/durableObjects/ChatRoom.server.ts
+++ b/app/durableObjects/ChatRoom.server.ts
@@ -314,9 +314,13 @@ export class ChatRoom extends Server<Env> {
 	}
 
 	onError(connection: Connection, error: unknown): void | Promise<void> {
+		log({
+			eventName: 'onErrorHandler',
+			error,
+		})
 		return this.getMeetingId().then((meetingId) => {
 			log({
-				eventName: 'onErrorHandler',
+				eventName: 'onErrorHandlerDetails',
 				meetingId,
 				connectionId: connection.id,
 				error,
@@ -348,7 +352,15 @@ export class ChatRoom extends Server<Env> {
 	async cleanupOldConnections() {
 		const meetingId = await this.getMeetingId()
 		if (!meetingId) log({ eventName: 'meetingIdNotFoundInCleanup' })
+		const websockets = this.ctx.getWebSockets()
 		const connections = [...this.getConnections()]
+		log({
+			eventName: 'cleaningUpConnections',
+			meetingId,
+			connectionsFound: connections.length,
+			websocketsFound: websockets.length,
+			websocketStatuses: websockets.map((w) => w.readyState),
+		})
 		const sessionsToCleanUp = await this.getUsers()
 
 		connections.forEach((connection) =>
diff --git a/app/utils/logging.ts b/app/utils/logging.ts
index c11094cc..cbddf06a 100644
--- a/app/utils/logging.ts
+++ b/app/utils/logging.ts
@@ -18,6 +18,13 @@ export type LogEvent =
 			meetingId?: string
 			connectionId: string
 	  }
+	| {
+			eventName: 'cleaningUpConnections'
+			meetingId?: string
+			connectionsFound: number
+			websocketsFound: number
+			websocketStatuses: number[]
+	  }
 	| {
 			eventName: 'userTimedOut'
 			meetingId?: string
@@ -41,6 +48,10 @@ export type LogEvent =
 	  }
 	| {
 			eventName: 'onErrorHandler'
+			error: unknown
+	  }
+	| {
+			eventName: 'onErrorHandlerDetails'
 			meetingId?: string
 			connectionId: string
 			error: unknown