email with attachments stuck in outbox

Emails are stuck in my outbox and will not send. I have been able to send email without attachments but as of today, for some reason, emails with attachments will not go out. I’ve had issues in the past opening email attachments and have noticed that is a bit problematic today as well but I am able to resolve it after closing and reopening emails.

Regardless, all of a sudden today I don’t seem to be able to send emails with attachments.

Using version 6.0.22609.0.

any assistance would be appreciated.

This might have something to do with the size of the attachment.  When this happened to me, I uploaded the file to the cloud and linked to it in the email.  If the attachment is a large image file, you could reduce its size.

Hello, what mail service are you using with eM Client? Are there any errors thrown by the application when you try to send out the message using your account? 

Regards,

The attachments are fairly small so size isn’t the problem. I am using micorsoft exchange / office 365. It seems to have resolved itself. I have outlook running on another machine at my home and had no errors but the issue persisted through the day with emclient through the day.

Hello, glad it works, we had an issue with some attachments download on Exchange servers, however we believe we were able to resolve this issue in a recent update, make sure you’re using this 6.0.22465.0 or later release of eM Client in order to avoid this issue in future.

The problem may have persisted in affected folders, thus after updating, make sure to re-sync (repair) the affected folders by navigating to the folder properties, available by right clicking the folder in the left pane.

Hope this helps,

I’m using 6.0.22609.0 and there don’t seem to be any updates. I’ll repair the folder as well. Thank you for the advice.

This version should already have the fix included, if the issue reoccurs perform a repair on the problematic folder and let me know if the issue persists.

Regards,

thank you.

Hi,

I’ve been experiencing the same problem periodically. It seems to be fine one day, then terrible the next. Today is one of the bad days. Like other have reported, emails with attachments get stuck in the “local folder/Outbox”. I’m using Office 365 mail server, Windows 7, EM Client V 6.0.24316.0

Thanks,

Hi John,
can you copy the error messages in Tools>Operations>Error when this happens, together with the Log from the third tab in the same Operations window?

Regards,
Olivia

Hi,

I have also been having this problem with my Exchange account called 5SAH. The error message is:

5SAH: Connecting to 5SAH failed
[Exchange Web Services] An attempt to connect to 5SAH failed. This could be cause by temporary server unavailability or incorrect settings. Do you want to check the settings?

The Log is below. Any help much appreciated!

Thanks,

Mark

14:36:14 Online state: changed to online due to NetworkAvailability

14:36:14 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/

14:36:14 Gmail [GData]  Synchronizing folder list

14:36:14 Gmail [GData]  Synchronizing folder list

14:36:14 5SAH [Exchange Web Services]  Synchronizing folder list

14:36:15 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Trash/’

14:36:15 Gmail [GData]  Synchronizing folder list

14:36:15 Gmail [GData]  Synchronizing folder list

14:36:15 Gmail [GData]  Synchronizing folder list

14:36:15 Gmail [IMAP]  Downloading message part…

14:36:15 Gmail [GData]  Synchronizing folder list

14:36:16 Gmail [IMAP]  Synchronizing subfolders: Done

14:36:16 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/Inbox

14:36:16 Gmail [GData]  Synchronizing folder ‘Gmail/Contacts/’

14:36:16 Gmail [IMAP]  Synchronizing subfolders: Done

14:36:16 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/[Gmail]

14:36:17 Gmail [GData]  Synchronizing folder ‘Gmail/Mark/’

14:36:17 Gmail [IMAP]  Downloading message part…: Done

14:36:17 Gmail [IMAP]  Downloading message part…

14:36:17 Gmail [IMAP]  Synchronizing subfolders: Done

14:36:17 Gmail [IMAP]  Synchronizing messages: For folder Gmail/Inbox

14:36:17 Gmail [IMAP]  Downloading message part…: Done

14:36:17 Gmail [IMAP]  Downloading message part…

14:36:17 Gmail [IMAP]  Synchronizing messages: For folder Gmail/Inbox

14:36:17 Gmail [IMAP]  Downloading message part…: Done

14:36:17 Gmail [IMAP]  Synchronizing messages: Done

14:36:20 Gmail [IMAP]  Synchronizing message flags: For folder Gmail/Inbox

14:36:21 Gmail [IMAP]  Synchronizing message flags: Done

14:36:22 Gmail [IMAP]  Downloading message part…

14:36:23 Gmail [IMAP]  Downloading message part…: Done

14:36:23 Gmail [IMAP]  Downloading message part…

14:36:23 Gmail [IMAP]  Downloading message part…: Done

14:36:23 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:36:45 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Sent/’

14:36:47 5SAH [Exchange Web Services]  Synchronizing folder list

14:36:47 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Trash/’

14:36:57 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Inbox/’

14:36:58 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:37:02 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Calendar/’

14:37:03 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Contacts/’

14:37:04 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Drafts/’

14:37:04 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Tasks/’

14:37:05 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Junk E-mail/’

14:37:05 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:37:09 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Outbox/’

14:37:13 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Sent/’

14:37:15 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/’

14:37:16 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

14:37:16 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Inbox/’

14:37:20 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Trash/’

14:37:23 Gmail [IMAP]  Synchronizing message flags: For folder Gmail/Inbox

14:37:24 Gmail [IMAP]  Synchronizing message flags: Done

14:39:38 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Inbox/’

14:39:39 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Inbox/’

14:39:40 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Inbox/’

14:39:41 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Inbox/’

14:39:42 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Inbox/’

14:39:43 5SAH [Exchange Web Services]  Uploading item(s) to folder ‘5SAH/Inbox/’

14:40:28 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/

14:40:28 5SAH [Exchange Web Services]  Synchronizing folder list

14:40:28 Gmail [GData]  Synchronizing folder list

14:40:28 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:40:29 Gmail [IMAP]  Synchronizing subfolders: Done

14:40:29 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/Inbox

14:40:29 Gmail [IMAP]  Synchronizing subfolders: Done

14:40:29 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/[Gmail]

14:40:30 Gmail [IMAP]  Synchronizing subfolders: Done

14:40:31 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Calendar/’

14:40:32 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Contacts/’

14:40:33 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Drafts/’

14:40:33 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Tasks/’

14:40:33 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Junk E-mail/’

14:40:34 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:40:37 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Outbox/’

14:40:38 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Sent/’

14:40:39 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/’

14:40:40 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

14:40:43 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

14:41:43 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

14:42:08 Gmail [GData]  Synchronizing folder list

14:42:09 Gmail [GData]  Synchronizing folder ‘Gmail/Contacts/’

14:42:43 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

14:43:09 5SAH [Exchange Web Services]  Sending email

14:43:09 5SAH [Exchange Web Services]  Sending email: Test

14:43:17 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/

14:43:17 Gmail [GData]  Synchronizing folder list

14:43:17 Gmail [GData]  Synchronizing folder list

14:43:18 Gmail [GData]  Synchronizing folder ‘Gmail/Contacts/’

14:43:18 Gmail [IMAP]  Synchronizing subfolders: Done

14:43:18 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/Inbox

14:43:19 Gmail [IMAP]  Synchronizing subfolders: Done

14:43:19 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/[Gmail]

14:43:19 Gmail [IMAP]  Synchronizing subfolders: Done

14:43:33 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/

14:43:33 Gmail [GData]  Synchronizing folder list

14:43:33 Gmail [GData]  Synchronizing folder list

14:43:34 Gmail [GData]  Synchronizing folder ‘Gmail/Contacts/’

14:43:34 Gmail [IMAP]  Synchronizing subfolders: Done

14:43:34 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/Inbox

14:43:34 Gmail [IMAP]  Synchronizing subfolders: Done

14:43:34 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/[Gmail]

14:43:35 Gmail [IMAP]  Synchronizing subfolders: Done

14:44:49 5SAH [Exchange Web Services]  MailExceptions.ConnectionException: The operation has timed out —> System.Net.WebException: The operation has timed out

14:44:49    at MailClient.Protocols.Exchange.ExchangeGenericCommand.Execute(WorkerStatus status)

14:44:49    — End of inner exception stack trace —

14:44:49    at MailClient.Protocols.Exchange.ExchangeGenericCommand.Execute(WorkerStatus status)

14:44:49    at MailClient.Commands.Command.Process(WorkerStatus status)

14:44:49 5SAH [Exchange Web Services]  Sending email: Test

14:44:49 5SAH [Exchange Web Services]  Synchronizing folder list

14:44:50 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:44:53 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Calendar/’

14:44:54 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Contacts/’

14:44:55 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Drafts/’

14:44:55 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Tasks/’

14:44:55 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Junk E-mail/’

14:44:56 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:44:59 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Outbox/’

14:45:00 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Sent/’

14:45:01 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/’

14:45:02 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

14:45:49 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

14:46:14 5SAH [Exchange Web Services]  Sending email

14:46:14 5SAH [Exchange Web Services]  Sending email: Test

14:46:14 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/

14:46:14 Gmail [GData]  Synchronizing folder list

14:46:14 Gmail [GData]  Synchronizing folder list

14:46:14 Gmail [IMAP]  Synchronizing subfolders: Done

14:46:14 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/Inbox

14:46:14 Gmail [GData]  Synchronizing folder ‘Gmail/Contacts/’

14:46:15 Gmail [IMAP]  Synchronizing subfolders: Done

14:46:15 Gmail [IMAP]  Synchronizing subfolders: For folder Gmail/[Gmail]

14:46:15 Gmail [IMAP]  Synchronizing subfolders: Done

14:47:54 5SAH [Exchange Web Services]  MailExceptions.ConnectionException: The operation has timed out —> System.Net.WebException: The operation has timed out

14:47:54    at MailClient.Protocols.Exchange.ExchangeGenericCommand.Execute(WorkerStatus status)

14:47:54    — End of inner exception stack trace —

14:47:54    at MailClient.Protocols.Exchange.ExchangeGenericCommand.Execute(WorkerStatus status)

14:47:54    at MailClient.Commands.Command.Process(WorkerStatus status)

14:47:54 5SAH [Exchange Web Services]  Sending email: Test

14:47:54 5SAH [Exchange Web Services]  Synchronizing folder list

14:47:55 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:47:58 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Calendar/’

14:47:58 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Contacts/’

14:47:59 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Drafts/’

14:47:59 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Tasks/’

14:48:00 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Junk E-mail/’

14:48:00 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Inbox/’

14:48:04 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Outbox/’

14:48:04 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Sent/’

14:48:05 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/’

14:48:06 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

14:48:54 5SAH [Exchange Web Services]  Synchronizing folder ‘5SAH/Trash/CBA/’

P.S. I am using eM Client version 6.0.24432.0

Hi Mark,
how big is the attachment you are trying to send?
And to what size do you have the attachment size limit set on your Exchange server?

Regards,
Olivia

Hi,

I’m also having a similar problem.

I’ve just upgraded to Version 7.0.24859.1 but this issue was also happening in the previous version 6.0.22609.0.

In my case, the emails with attachments seem to send alright (I’ve had confirmation from the recipients that they’ve received them). It’s just that the emails remain in the “Outbox” folder and don’t transfer to the “Sent” folder. The latest two had attachment sizes of 249KB and 2.283MB respectively, so not that big. I’ve sent much larger attachments in the past so it can’t be the size. This doesn’t happen to emails without attachments.

I note a previous comment where it’s suggested that “…after updating, make sure to re-sync (repair) the affected folders by navigating to the folder properties, available by right clicking the folder in the left pane.” I’ve tried that but the properties window that appears just has “OK” and “Cancel” on it. There is no facility to sync (repair) the folder.

I also notice that sometimes (not always) an “Operations” message comes up stating “[SMTP] An attempt to connect to ***@****.com failed. This could be caused by temporary server unavailability or incorrect settings. Do you want to check the settings?” When I check the settings, they are correct.

Anyone have any ideas?

Regards,

David.

Hi David,
when the error pops up, please copy the content of the Tools>Operations>Log.
Also send me a screenshot of the Properties window for the folder, because there should be a repair tab in it.

Regards,
Olivia

Hi Olivia,

I cleared the log and fired off a test email to one of my other addresses. The contents of the Log are below:

15:04:54 acdc@cujimmy.plus.com [SMTP]  Connecting: To acdc@cujimmy.plus.com15:04:56 acdc@cujimmy.plus.com [SMTP]  Connected: To acdc@cujimmy.plus.com
15:04:56 acdc@cujimmy.plus.com [SMTP]  Sending messages
15:05:14 acdc@cujimmy.plus.com [POP3]  Connecting: To acdc@cujimmy.plus.com
15:05:14 david.cottier@gmail.com [IMAP]  Synchronizing subfolders: For folder david.cottier@gmail.com/
15:05:14 david.cottier@gmail.com [Google Contacts]  Synchronizing folder list
15:05:14 david.cottier@gmail.com [Google Contacts]  Synchronizing folder ‘david.cottier@gmail.com/Contacts/’
15:05:15 david.cottier@gmail.com [IMAP]  Synchronizing subfolders: Done
15:05:15 david.cottier@gmail.com [IMAP]  Synchronizing subfolders: For folder david.cottier@gmail.com/INBOX
15:05:17 david.cottier@gmail.com [IMAP]  Synchronizing subfolders: Done
15:05:17 david.cottier@gmail.com [IMAP]  Synchronizing subfolders: For folder david.cottier@gmail.com/[Gmail]
15:05:17 acdc@cujimmy.plus.com [POP3]  Connected: To acdc@cujimmy.plus.com
15:05:18 david.cottier@gmail.com [IMAP]  Synchronizing subfolders: Done
15:05:19 acdc@cujimmy.plus.com [POP3]  Downloading messages: From acdc@cujimmy.plus.com
15:05:26 acdc@cujimmy.plus.com [SMTP]  MailClient.Accounts.SocketException: Sending messages failed due to the following reason: 
15:05:26     “Unable to read data from the transport connection: A connection attempt failed because the connected party did not properly respond after a period of time, or established connection failed because connected host has failed to respond.”
15:05:26    at MailClient.Protocols.Smtp.SmtpSendCommand.Execute(WorkerStatus status)
15:05:26    at MailClient.Commands.Command.Process(WorkerStatus status)
15:05:27 acdc@cujimmy.plus.com [POP3]  Disconnected: From acdc@cujimmy.plus.com
15:05:27 acdc@cujimmy.plus.com [POP3]  Disconnected: Done
15:06:07 david.cottier@gmail.com [IMAP]  Synchronizing messages: For folder david.cottier@gmail.com/[Gmail]/All Mail
15:06:08 david.cottier@gmail.com [IMAP]  Synchronizing messages: Done

I also enclose a screenshot of the Properties window for the Outbox Folder. Hopefully that will help.

Regards,
David

Hello, is anyone there?

Hello David,
can you try making and exception in your windows firewall and anti-virus software for eM Client?

Regards,
Olivia

Hi Olivia,

I checked my Kaspersky Internet Security 2016 Applications Manager and eMClient has no restrictions on it.

I sent a test email with attachment (Mail Anti-Virus was ON) to another of my addresses and it arrived ok but still remains in my Outbox. I then sent a second test email with attachment (Mail Anti-Virus turned OFF) which I don’t think sent because I haven’t received it at my other address yet. It is also still hanging around my Outbox.

Every so often, I try to send them again from my Outbox and the Operations window shows the process happening but still the 2nd email hasn’t sent or arrived and they are both still remaining in the Outbox.

Regards,
David

I have problems sending attachments above a few kb, NONE of the questions on this forum for this issue have been answered!!!