(2023-07-15, 01:25 AM)hov Wrote: Hello I currently have issues with SMTP and webhook for Jellyfin. I currently have my SMTP server url, my email account I want to connect to webhook to send out the notification emails but it doesn't seem to be working. Below are my logs around the time of playback + screenshots of my webhook settings. What is webhook url for email?

Code:

[2023-07-14 18:03:20.691 -07:00] [INF] [34] Jellyfin.Api.Helpers.MediaInfoHelper: User policy for "user1". EnablePlaybackRemuxing: True EnableVideoPlaybackTranscoding: True EnableAudioPlaybackTranscoding: True
[2023-07-14 18:03:20.692 -07:00] [INF] [34] Jellyfin.Api.Helpers.MediaInfoHelper: StreamBuilder.BuildVideoItem( Profile="Jellyfin Media Player", Path="/14TB/downloads/TV/Conan.Without.Borders.S01.1080p.HMAX.WEB-DL.DD2.0.H.264-WELP/Conan.Without.Borders.S01E01.Conan.in.Cuba.1080p.HMAX.WEB-DL.DD2.0.H.264-WELP.mkv", AudioStreamIndex=null, SubtitleStreamIndex=null ) => ( PlayMethod=DirectPlay, TranscodeReason=0 ) "media:/videos/79b4f77e-ad4b-f9c0-a6aa-0cfa99a42c9b/stream.mkv?MediaSourceId=79b4f77ead4bf9c0a6aa0cfa99a42c9b&Static=true&VideoCodec=h264&AudioCodec=ac3&AudioStreamIndex=1&api_key=<token>&Tag=58e6a715c19049fe295117ed768114d1"
[2023-07-14 18:03:31.795 -07:00] [INF] [35] Jellyfin.Api.Helpers.MediaInfoHelper: User policy for "user1". EnablePlaybackRemuxing: True EnableVideoPlaybackTranscoding: True EnableAudioPlaybackTranscoding: True
[2023-07-14 18:03:31.795 -07:00] [INF] [35] Jellyfin.Api.Helpers.MediaInfoHelper: StreamBuilder.BuildVideoItem( Profile="Jellyfin Media Player", Path="/14TB/downloads/TV/Conan.Without.Borders.S01.1080p.HMAX.WEB-DL.DD2.0.H.264-WELP/Conan.Without.Borders.S01E09.Conan.in.Italy.1080p.HMAX.WEB-DL.DD2.0.H.264-WELP.mkv", AudioStreamIndex=null, SubtitleStreamIndex=null ) => ( PlayMethod=DirectPlay, TranscodeReason=0 ) "media:/videos/5de4041b-6f67-6ecf-abc2-e21241806997/stream.mkv?MediaSourceId=5de4041b6f676ecfabc2e21241806997&Static=true&VideoCodec=h264&AudioCodec=ac3&AudioStreamIndex=1&api_key=<token>&Tag=e9e29932401685e8569cba8585349c27"
[2023-07-14 18:03:44.131 -07:00] [INF] [44] Emby.Server.Implementations.ScheduledTasks.TaskManager: "IntervalTrigger" fired for task: "Webhook Item Added Notifier"
[2023-07-14 18:03:44.131 -07:00] [INF] [44] Emby.Server.Implementations.ScheduledTasks.TaskManager: Queuing task "ItemAddedScheduledTask"
[2023-07-14 18:03:44.131 -07:00] [INF] [49] Emby.Server.Implementations.ScheduledTasks.TaskManager: Executing "Webhook Item Added Notifier"
[2023-07-14 18:03:44.132 -07:00] [INF] [49] Emby.Server.Implementations.ScheduledTasks.TaskManager: "Webhook Item Added Notifier" Completed after 0 minute(s) and 0 seconds
[2023-07-14 18:03:44.132 -07:00] [INF] [49] Emby.Server.Implementations.ScheduledTasks.TaskManager: ExecuteQueuedTasks
[2023-07-14 18:03:53.456 -07:00] [INF] [46] Emby.Server.Implementations.HttpServer.WebSocketManager: WS "192.168.1.175" closed
[2023-07-14 18:03:53.761 -07:00] [INF] [47] Emby.Server.Implementations.HttpServer.WebSocketManager: WS "192.168.1.175" request
[2023-07-14 18:04:09.587 -07:00] [WRN] [48] Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient: Error sending email
System.TimeoutException: The operation has timed out.
  at MailKit.Net.SocketUtils.ConnectAsync(String host, Int32 port, IPEndPoint localEndPoint, Int32 timeout, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.MailService.ConnectNetwork(String host, Int32 port, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.Net.Smtp.SmtpClient.ConnectAsync(String host, Int32 port, SecureSocketOptions options, Boolean doAsync, CancellationToken cancellationToken)
  at Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient.SendAsync(SmtpOption option, Dictionary`2 data)
[2023-07-14 18:04:09.603 -07:00] [WRN] [44] Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient: Error sending email
System.TimeoutException: The operation has timed out.
  at MailKit.Net.SocketUtils.ConnectAsync(String host, Int32 port, IPEndPoint localEndPoint, Int32 timeout, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.MailService.ConnectNetwork(String host, Int32 port, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.Net.Smtp.SmtpClient.ConnectAsync(String host, Int32 port, SecureSocketOptions options, Boolean doAsync, CancellationToken cancellationToken)
  at Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient.SendAsync(SmtpOption option, Dictionary`2 data)
[2023-07-14 18:04:09.617 -07:00] [WRN] [39] Jellyfin.Server.Middleware.ResponseTimeMiddleware: Slow HTTP Response from "http://192.168.1.100:8096/Sessions/Capabilities/Full" to "192.168.1.175" in 0:02:00.1902146 with Status Code 204
[2023-07-14 18:04:09.624 -07:00] [INF] [28] Emby.Server.Implementations.HttpServer.WebSocketManager: WS "192.168.1.175" closed
[2023-07-14 18:04:14.130 -07:00] [INF] [28] Emby.Server.Implementations.ScheduledTasks.TaskManager: "IntervalTrigger" fired for task: "Webhook Item Added Notifier"
[2023-07-14 18:04:14.130 -07:00] [INF] [28] Emby.Server.Implementations.ScheduledTasks.TaskManager: Queuing task "ItemAddedScheduledTask"
[2023-07-14 18:04:14.130 -07:00] [INF] [28] Emby.Server.Implementations.ScheduledTasks.TaskManager: Executing "Webhook Item Added Notifier"
[2023-07-14 18:04:14.131 -07:00] [INF] [28] Emby.Server.Implementations.ScheduledTasks.TaskManager: "Webhook Item Added Notifier" Completed after 0 minute(s) and 0 seconds
[2023-07-14 18:04:14.131 -07:00] [INF] [28] Emby.Server.Implementations.ScheduledTasks.TaskManager: ExecuteQueuedTasks
[2023-07-14 18:04:39.524 -07:00] [WRN] [46] Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient: Error sending email
System.TimeoutException: The operation has timed out.
  at MailKit.Net.SocketUtils.ConnectAsync(String host, Int32 port, IPEndPoint localEndPoint, Int32 timeout, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.MailService.ConnectNetwork(String host, Int32 port, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.Net.Smtp.SmtpClient.ConnectAsync(String host, Int32 port, SecureSocketOptions options, Boolean doAsync, CancellationToken cancellationToken)
  at Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient.SendAsync(SmtpOption option, Dictionary`2 data)
[2023-07-14 18:04:39.734 -07:00] [WRN] [50] Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient: Error sending email
System.TimeoutException: The operation has timed out.
  at MailKit.Net.SocketUtils.ConnectAsync(String host, Int32 port, IPEndPoint localEndPoint, Int32 timeout, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.MailService.ConnectNetwork(String host, Int32 port, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.Net.Smtp.SmtpClient.ConnectAsync(String host, Int32 port, SecureSocketOptions options, Boolean doAsync, CancellationToken cancellationToken)
  at Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient.SendAsync(SmtpOption option, Dictionary`2 data)
[2023-07-14 18:04:39.795 -07:00] [WRN] [38] Jellyfin.Server.Middleware.ResponseTimeMiddleware: Slow HTTP Response from "http://192.168.1.100:8096/Sessions/Playing/Progress" to "192.168.1.175" in 0:02:00.0714248 with Status Code 204
[2023-07-14 18:04:44.130 -07:00] [INF] [28] Emby.Server.Implementations.ScheduledTasks.TaskManager: "IntervalTrigger" fired for task: "Webhook Item Added Notifier"
[2023-07-14 18:04:44.130 -07:00] [INF] [28] Emby.Server.Implementations.ScheduledTasks.TaskManager: Queuing task "ItemAddedScheduledTask"
[2023-07-14 18:04:44.130 -07:00] [INF] [33] Emby.Server.Implementations.ScheduledTasks.TaskManager: Executing "Webhook Item Added Notifier"
[2023-07-14 18:04:44.130 -07:00] [INF] [33] Emby.Server.Implementations.ScheduledTasks.TaskManager: "Webhook Item Added Notifier" Completed after 0 minute(s) and 0 seconds
[2023-07-14 18:04:44.130 -07:00] [INF] [33] Emby.Server.Implementations.ScheduledTasks.TaskManager: ExecuteQueuedTasks
[2023-07-14 18:04:46.631 -07:00] [WRN] [33] Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient: Error sending email
System.TimeoutException: The operation has timed out.
  at MailKit.Net.SocketUtils.ConnectAsync(String host, Int32 port, IPEndPoint localEndPoint, Int32 timeout, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.MailService.ConnectNetwork(String host, Int32 port, Boolean doAsync, CancellationToken cancellationToken)
  at MailKit.Net.Smtp.SmtpClient.ConnectAsync(String host, Int32 port, SecureSocketOptions options, Boolean doAsync, CancellationToken cancellationToken)
  at Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient.SendAsync(SmtpOption option, Dictionary`2 data)
[2023-07-14 18:04:46.663 -07:00] [WRN] [3] Jellyfin.Server.Middleware.ResponseTimeMiddleware: Slow HTTP Response from "http://192.168.1.100:8096/Sessions/Playing/Progress" to "192.168.1.175" in 0:02:00.0441665 with Status Code 204
[2023-07-14 18:04:51.119 -07:00] [INF] [3] Emby.Server.Implementations.HttpServer.WebSocketManager: WS "192.168.1.175" closed
[2023-07-14 18:04:51.200 -07:00] [WRN] [40] Jellyfin.Plugin.Webhook.Destinations.Smtp.SmtpClient: Error sending email

(2023-07-15, 02:01 AM)TheDreadPirate Wrote: Looks like a standard 30 second timeout.  Whatever your email server is running on, have the firewall rules been added to allow the traffic through on port 465?

(2023-07-15, 02:28 AM)TheDreadPirate Wrote: Wherever these emails are supposed to go, they are not arriving.  Not due to any issue on the Jellyfin server's end, I don't think.  No acknowledgement one way or the other.  The connection is just timing out.  Is taylor.mxrouting.net a local machine or remote?

(2023-07-15, 05:30 AM)TheDreadPirate Wrote: Do you know if Thunderbird is using plain SSL (465) or STARTTLS (587)?  ....Unencrypted (25)?  I hope not.  I'm not sure how that would translate if it was STARTTLS in the webhook plugin.  Change to port 587, uncheck Use SSL?