Email Notifications not working

[ITGuy1024 13]

2022-09-19 08:29:48.931 Info Server: http/1.1 POST http://172.30.1.109:8096/emby/Notification/SMTP/Test/5644d3e530a747209eea339361fddf97?X-Emby-Client=Emby Web&X-Emby-Device-Name=Chrome Windows&X-Emby-Device-Id=4c88c7ed-4137-4910-bdd7-e9295282d7ec&X-Emby-Client-Version=4.7.6.0. UserAgent: Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/105.0.0.0 Safari/537.36
2022-09-19 08:29:48.931 Info App: Sending email myemailaddress@gmail.com with subject Emby: Emby: Test Notification
2022-09-19 08:29:54.476 Debug Server: http/1.1 GET http://172.30.1.109:8096/emby/System/Logs/embyserver.txt. UserAgent: Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/105.0.0.0 Safari/537.36
2022-09-19 08:29:55.542 Debug Server: http/1.1 Response 200 to host15. Time: 1066ms. http://172.30.1.109:8096/emby/System/Logs/embyserver.txt
2022-09-19 08:29:57.474 Debug App: Ping test result to http://172.30.1.109:8096/system/ping. Success: True
2022-09-19 08:29:57.657 Error App: Error sending email: System.Net.Mail.SmtpException: Syntax error, command unrecognized. The server response was: 
   at System.Net.Mail.SmtpConnection.ConnectAndHandshakeAsyncResult.End(IAsyncResult result)
   at System.Net.Mail.SmtpClient.ConnectCallback(IAsyncResult result)
--- End of stack trace from previous location ---
   at MediaBrowser.Plugins.SmtpNotifications.Notifier.SendNotification(UserNotification request, CancellationToken cancellationToken) 
2022-09-19 08:29:57.657 Info Server: http/1.1 Response 204 to host15. Time: 10049ms. http://172.30.1.109:8096/emby/Notification/SMTP/Test/5644d3e530a747209eea339361fddf97?X-Emby-Client=Emby Web&X-Emby-Device-Name=Chrome Windows&X-Emby-Device-Id=4c88c7ed-4137-4910-bdd7-e9295282d7ec&X-Emby-Client-Version=4.7.6.0
2022-09-19 08:29:58.345 Error App: Error sending email: System.Net.Mail.SmtpException: Syntax error, command unrecognized. The server response was: 
   at System.Net.Mail.SmtpConnection.ConnectAndHandshakeAsyncResult.End(IAsyncResult result)
   at System.Net.Mail.SmtpClient.ConnectCallback(IAsyncResult result)
--- End of stack trace from previous location ---
   at MediaBrowser.Plugins.SmtpNotifications.Notifier.SendNotification(UserNotification request, CancellationToken cancellationToken) 
2022-09-19 08:29:58.345 Info Server: http/1.1 Response 204 to host15. Time: 10039ms. http://172.30.1.109:8096/emby/Notification/SMTP/Test/5644d3e530a747209eea339361fddf97?X-Emby-Client=Emby Web&X-Emby-Device-Name=Chrome Windows&X-Emby-Device-Id=4c88c7ed-4137-4910-bdd7-e9295282d7ec&X-Emby-Client-Version=4.7.6.0
2022-09-19 08:29:58.573 Error App: Error sending email: System.Net.Mail.SmtpException: Syntax error, command unrecognized. The server response was: 
   at System.Net.Mail.SmtpConnection.ConnectAndHandshakeAsyncResult.End(IAsyncResult result)
   at System.Net.Mail.SmtpClient.ConnectCallback(IAsyncResult result)
--- End of stack trace from previous location ---
   at MediaBrowser.Plugins.SmtpNotifications.Notifier.SendNotification(UserNotification request, CancellationToken cancellationToken) 
2022-09-19 08:29:58.573 Info Server: http/1.1 Response 204 to host15. Time: 10027ms. http://172.30.1.109:8096/emby/Notification/SMTP/Test/5644d3e530a747209eea339361fddf97?X-Emby-Client=Emby Web&X-Emby-Device-Name=Chrome Windows&X-Emby-Device-Id=4c88c7ed-4137-4910-bdd7-e9295282d7ec&X-Emby-Client-Version=4.7.6.0
2022-09-19 08:29:58.787 Error App: Error sending email: System.Net.Mail.SmtpException: Syntax error, command unrecognized. The server response was: 
   at System.Net.Mail.SmtpConnection.ConnectAndHandshakeAsyncResult.End(IAsyncResult result)
   at System.Net.Mail.SmtpClient.ConnectCallback(IAsyncResult result)
--- End of stack trace from previous location ---
   at MediaBrowser.Plugins.SmtpNotifications.Notifier.SendNotification(UserNotification request, CancellationToken cancellationToken) 
2022-09-19 08:29:58.787 Info Server: http/1.1 Response 204 to host15. Time: 10036ms. http://172.30.1.109:8096/emby/Notification/SMTP/Test/5644d3e530a747209eea339361fddf97?X-Emby-Client=Emby Web&X-Emby-Device-Name=Chrome Windows&X-Emby-Device-Id=4c88c7ed-4137-4910-bdd7-e9295282d7ec&X-Emby-Client-Version=4.7.6.0
2022-09-19 08:29:59.651 Error App: Error sending email: System.Net.Mail.SmtpException: Syntax error, command unrecognized. The server response was: 
   at System.Net.Mail.SmtpConnection.ConnectAndHandshakeAsyncResult.End(IAsyncResult result)
   at System.Net.Mail.SmtpClient.ConnectCallback(IAsyncResult result)

 

 

2022-09-19 08:38:50.197 Info Server: http/1.1 POST http://172.30.1.109:8096/emby/Notification/SMTP/Test/5644d3e530a747209eea339361fddf97?X-Emby-Client=Emby Web&X-Emby-Device-Name=Chrome Windows&X-Emby-Device-Id=4c88c7ed-4137-4910-bdd7-e9295282d7ec&X-Emby-Client-Version=4.7.6.0. UserAgent: Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/105.0.0.0 Safari/537.36
2022-09-19 08:38:50.198 Info App: Sending email myemail@gmail.com with subject Emby: Emby: Test Notification
2022-09-19 08:38:52.546 Error App: Error sending email: System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.0 Authentication Required. Learn more at
   at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
   at System.Net.Mail.MailCommand.EndSend(IAsyncResult result)
   at System.Net.Mail.SendMailAsyncResult.SendMailFromCompleted(IAsyncResult result)
--- End of stack trace from previous location ---
   at System.Net.Mail.SendMailAsyncResult.End(IAsyncResult result)
   at System.Net.Mail.SmtpClient.SendMailCallback(IAsyncResult result)

Version 4.7.6.0
Emby Premier Member

Is this related to Google removing the "allow  less secure apps" feature?

Edited September 19, 2022 by ITGuy1024

[Luke 37094]

Hi, yes, the email plugin is currently not going to work with Gmail.

[AxeMan 22]

HI @Luke any update on this? 

 

I have 2FA turn on my account - and have assigned an app password for Emby- as I'd seen some issues in other apps that were sending emails via Gmail. Everything else seems to work fine, via port 465, w. app password. 

 

Thanks!

[Luke 37094]

42 minutes ago, AxeMan said:

HI @Luke any update on this? 

 

I have 2FA turn on my account - and have assigned an app password for Emby- as I'd seen some issues in other apps that were sending emails via Gmail. Everything else seems to work fine, via port 465, w. app password. 

 

Thanks!

I don't have an update at this time. The limitation is in the .net runtime email messaging api. We'd have to roll our own entirely in order to resolve this.

[ITGuy1024 13]

Hopefully this will help others. I got the email plugin to work with a 2FA account.

If you have 2FA turned on go here https://myaccount.google.com/apppasswords

Setup an app password for emby and use that password with the email you're trying to use for sending emails.

[Luke 37094]

6 minutes ago, ITGuy1024 said:

Hopefully this will help others. I got the email plugin to work with a 2FA account.

If you have 2FA turned on go here https://myaccount.google.com/apppasswords

Setup an app password for emby and use that password with the email you're trying to use for sending emails.

Thanks for sharing.