Geary cannot send mail with attachments

I've been using Geary, a mail client, and I've never been able to send any mail containing attachments. The same mail, meanwhile, gets through if I use Thunderbird. The exact messages which Geary posts if I run it through a terminal are:
** Message: smtp-client-session.vala:80: Unable to QUIT: Error writing data to TLS socket: The specified session has been invalidated for some reason.
** Message: smtp-client-session.vala:88: Unable to disconnect: Unable to shutdown socket: Transport endpoint is not connected
These two messages keep repeating. There is no problem with mails not containing attachments. Has anyone else had the same problem? Or is this a bug I should be reporting upstream?

Perhaps the mail server has a size limit that it allows. Might try a free web service and see if that will work for those attachments.

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Cannot send mail with attachments-plain mail its ok. Any ideas?

Out of the blue I cannot send e-mails with attachments (any kind). Mail without attachments go out without problems.
Very weird.
I have an iMac, mac mail 5.2. and Lion.
Please help.
Thanks

Perhaps the mail server has a size limit that it allows. Might try a free web service and see if that will work for those attachments.

Cannot send mail with attachments after 3.0

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I am also having this problem. Mine keeps saying that it can't connect to the SMTP server that I have turned off. I was told by Apple that I had to use the AT&T SMTP server which fixed my problem before. However, I downloaded 3.0 yesterday and now it refuses to even try the AT&T server even though it's the only one I have turned on. I can send text emails without any issue.

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Receiving mail, but can't send mail with attachments?

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I can't send mails anymore, I have been able to send some without any attachments (i.e. reply doesn't work as it automatically attaches the original text). This started 3 days ago. Also, my mail doesn't seem to recognize powerpoint and word docs., but I a know the people who have send me such files do not have VISTA. When I choose "open with" then it works. So I have 2 problems, one being moe urgent then the other.
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Try going into Settings > Mail, Contacts, Calendars > select the account > account name , tap on SMTP (under the 'Outgoing Mail Server' heading) and then tap on your Primary Server and try entering your email account and password and see if it then works

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Thanks in advance

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http://www.oracle.com/technology/sample_code/tech/pl_sql/htdocs/Utl_Smtp_Sample.html
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Problem sending mail with attachments???

Hi Everybody,
I have got a problem sending mail with attachments...
I am able to send a plain mail ... but when i am trying to send mail along with an attachment ... its not being sent....
its not showing any error it is simply hanging...
what should i do?
If u know any solns please do suggest me....
Thanks in advance

activation.jar is already there...
initially i wrote a swing program as a front end and it was working abs fine... in my sense it was properly sending mails along with the attachments...
when i changed the front-end to JSP handled by Servlets i am getting a problem...
and even the swing program stopped working ...
now swing program is getting compiled but it is hanging at run time showing an exception "Exception occured during event dispatching"
i dont understand what probably may be the problem...
if u can trace out, please give me any suggestions
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In Exchange 2013 i cannot open mails with attachments greater than 19.6 MB in EWS or OWA

Hello,
i have in Exchange 2013 CU3 on Windows 2012 the following problem :
When backup mails using EWS i get the message " EWS Error Code : ErrorMessageSizeExceeded." in mails with attachments greater than 20.137 KB ( 19.6 MB).
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Thanks in advance

Hi,
To change the maximum message size for Outlook Web App clients, you need to change the value of
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maxReceivedMessageSize by editing %ExchangeInstallPath%ClientAccess\Owa\web.config in notepad.
To change the maximum message size for Exchange Web Services clients, you need to change the value of
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When you are finished, save and close the Web.config file. Also need to restart IIS by running the following command:
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For more information about Configure Client-Specific Message Size Limits on Client Access Servers, please refer to:
http://technet.microsoft.com/en-us/library/hh529949(v=exchg.150).aspx
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Winnie Liang
TechNet Community Support

Cannot move mail with attachments

I was helping a friend prepare to eventually delete her hotmail account from Mail on her iPad. She did not want to lose any mails, so we were moving messages from her hotmail inbox to her gmail inbox. Moving the messages was uneventful until we came to messages with attachments. Any mails with attachments will not move. When trying to do so, we get an error message that simply says the mails cannot be moved...but gave no reason why (really helpful). They're simply stuck in the hotmail Inbox and cannot be moved out. Anybody have a clue what's happening here?
In a worse case scenario I told her we could forward those messages to her new account and then just delete them from her hotmail account. By doing so we'll save the messages, but the messages won't appear in the new inbox according to when they were originally sent, but rather by when they were forwarded. Being able to move them would be the proper solution, but it simply won't work.

Perhaps the mail server has a size limit that it allows. Might try a free web service and see if that will work for those attachments.

Cannot send mail with mavericks

Hi I'm using an iMac 2011 27 in. Shawcable is my ISP. I can receive mail. I cannot send mail. I get the error "cannot connect to account myaccount, enter password for user myname" If I go into accounts in mail prefs all smtp accounts show as offline. I have been over all my settings with shaw they say problem is on my end. They say my computer isn't connecting. Anyone have any ideas?
jmickey42

Without in details on what you have tried, I'll throw out some things:
On the SMTP server settings, use a custom port number instead of using the default ports.
Make sure you don't have any firewall, net-nanny, or other such network blockers running.
In Mail, Open Connection Doctor from the Window menu.
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Iphone - cant send mails with attachments

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We run exchange 2007 & I have my account setup on my iphone but mails with attachments wont send they just sit in the outbox. Now other users in job have nokia E63 which they can send attachments without problems.
Both would use activesync but presume maybe in a different way & that i just might need to make some change on exhange.
Anyone have any ideas?

Turns out a couple of components of AVG were causing the problem. Please see http://www.avg.com/us-en/faq?num=3254#tba7

Cannot send mail with mobile mail software

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From working with other customers, the best thing to do would be to remove the email account entirely from the Mobile Email program and re-add it. If the issue persists, remove the Mobile Email application altogether and redownload it. If it still persists even after that and all other data services are working such as the browser, My Verizon, etc. call AOL Mobile Support at 866-265-3019.
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Cannot send messages with attachments

I recently got a new 13" MacBook Pro with Snow Leopard. I setup Mail to work with our OWA Exchange Server and it works fine except for one major bug. I cannot send ANY messages that have attachments. Here's what I've tried so far to resolve the issue:
Tried a smaller attachment - no change
Tried a larger attachment - no change
Tried composing a new message - no change
Tried replying to a message - no change
Tried forwarding a message - no change
Tried different types of attachments (Word docs, pdfs, jpgs, etc) - no change
Updated to the OS to 10.6.1 - no change
What else can I try?

Right, forgot that part. It goes away for one second (as if the message has been sent), then comes back with this error:
Cannot send message using the server +(my smtp server settings)+. The Exchange 2007 connection to server +(our exchange server's ip address)+ failed. Select a different outgoing mail server from the list below or click Try Later to leave the message in your Outbox until it can be sent.
Below that, I get a list of SMTP servers, but since I only use one account with Mail, its just the Exchange entry. There are three button across the bottom: Edit Message, Try Layer, and Try With Selected Server.
If I select my Exchange server and click Try With Selected Server, it comes right back with this same error.
If I click Try Later, it puts in the Outbox, but never sends it. I left a message in there for a day once and it eventually gave me this error again for that message.
If I click Edit Message, and remove the attachment, I'm able to send the message.
My guess is that Mail isn't encoding the attachments correctly, which means I'll have to wait for Apple to fix the bug.

Mail doesn't send mails with attachments 1Mb

Hi,
I'm using Mail with a ManagedExchange account. Before Snow Leopard I was using Entourage 2008.
Everything seems to work fine. Except sending of larger files fails.
Every time I send a mail which is approx. <1Mb Mail starts transmitting data (see it via Little Snitch 2.2b) and stops after a while doing nothing anymore. The mail stays in the outbox, and the moving circle which indicates that a folder is being synchronized appears endless. No other mails are going out then. After a while I get a message that my email couldn't be sent via my mail server. And the connection failed. And I can choose another mail server if I would have any. Entourage doesn't have that problems. So the connection seems to be fine. Small attachments are no problem.
What's the problem?
Regards,
OberMufti

I'm getting a similar problem. Snow Leopard Mail for me seems to be choking on large attachments - sending them, forwarding them, or even moving them from one IMAP folder to another.
My mails are getting through, but it takes a long time and they are dragging the whole system to a crawl in the process.

Sending mails with attachments is sending some parts in HTM format

I have configured my ME account to Apple Mail. When I send an email with first some text, then i add an picture under the text, and after the picture i add some more text. Then i send the mail to someone.
When that person opens the mail in Outlook on Windows for example, the first text that i typed above the picture is visible in the mail, the picture is added as an jpg attachment, but the text that i typed under the picture is always added in a HTM file
So they don't see the whole mail, only the first end until the picture, the rest is an HTM attachment.
It happens with mails send with Mobile Me, but also with other POP3 accounts.
I already tried to change EDIT - ATTACHMENTS - SEND AS WINDOWS ATTACHMENTS and ATTACHMENTS AT END OF THE MAIL
Both settings doesn't work.
Please HELP!!

I was troubleshooting my own issue noted above and tried to send the attachments via gmail's web interface (bypassing Apple Mail). This time, gmail provided an error message stating that the file contained a virus.
Since it was a zip of several Word docs, I saved them as PDFs and then rezipped, and Apple Mail sent them off like a champ.
Evidently, Mail does not have a method for relaying the precise nature of the error message that gmail sends (in this case that the attachment had what gmail thought was a virus). This would be a prime area for some software developers to tackle on a future version of Mail.
By the way, the files almost certainly do not contain viruses; they are extremely old Word Docs that have been on my successive Mac hard drives for at least 9 years. Too old a format for gmail to recognize?
Hope this helps someone who may be having the same trouble.

Geary cannot send mail with attachments

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