OS X V10.6 Snow Leopard :: Mail Not Sending Attachments

May 2, 2012

On behalf of a friend who I usually do phone support for when he has a problem.

Mail 4.5 (1084)

Mac OSX 10.6.8

He has mail set to access Gmail (IMAP) and it works fine when sending a normal email, however, when sending an attachment, the activity monitor, goes halfway and then the reate drops off and the mesage about cannot be sent from this outgoing server is displayed. - mesage goes to outbox. - Open that message back up, delete the attachment and send, it goes no problems.

Tried to work out what the problem is, by:checking Gmail (with attachments) through browser, sent OKtrying different file types, jpg, txt, zip, and different ways of attaching them, either from menu or dragging them into the meassga pain. - No sendrepair permissions for mac, incase any pref files corrupt. - No sendbrand new jpg created from photoshop - No sendimage emailed from me, copied to desktop and then sent back to me - No send

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OS X V10.5 Leopard :: Apple Mail Combined With Imap Gmail Not Sending Attachments?

May 6, 2012

I have been working quite happily with Mail and an imap gmail account for a couple of years until recently.  Now I can no longer send attachments and if I try to forward an email that has a bit going on in it like a group-on email or something similar it won't send that either.  I get a message Cannot send message using the server [URL]:(my emailaddress)[URL]Sending the message content to the server failed I have searched for answers all over the net, have tried google help pages that suggest I remove my email address from the outgoing server details but NOTHING works. Today I finally gave up on Apple Mail and tried entourage - same result in that I couldn't send anything with attachements but a different error message. 

I hadn't changed anything when it stopped working and it can't be the settings because every now and then I get an attachment through.  There is lots on the net but I haven't found anything that works or all the stuff I am reading is really old. and also, just to finally drive me over the edge I got sent an email with an attachment today that didn't come through onto my mac.  If I go onto gmail via safari there is my attachment.  In Mail, it doesn't even give me a hint that it's there

Info:
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Mar 20, 2009

I am running 10.4.11 with the mail program that is installed which is 2.1.3.

My daughter in college has a MacBook Pro Intel running 10.5.x and uses the college mail program (site).

Every attachment that I send her that as a jpg, she says downloads to her desk top as a .acs ( I believe) which she can't open to view. If she goes to a windows computer with the same college e-mail site she can view them.

Question: what can be done to send/receive these so they can be viewed as jps's on her computer? Would send them as windows friendly attachments help?

I'm guessing that the e-mail site is probably set up for more windows friendly than Mac friendly.

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OS X Mavericks :: (10.9.5) Mail Not Sending Attachments

Dec 3, 2014

Using Apple Mail on OS X 10.9.  

My workplace is an Apple environment. Shortly after some of the iMacs were upgraded to 10.9 we've had some trouble with Mail. The main issue is Mail is not sending the attached image or file. On one of the iMacs that sends a lot of email with attachments, I removed the email account and added it back. After doing this this account is able to send attachments (how long this fix will last I don't know), however, a particular email we tried to send did not send the attached files.  

After hearing about this issue I sent several test emails from this iMac and had mixed results. Sending just the attachments would work. Sending the attachments and text would only send the text. I have tried dragging the images from the Desktop into the message. I have used the attachment button and made sure Windows Friendly Attachments was checked. 

I hand-typed a paragraph of the original email and sent it with the attachments and that email worked. I think it could be something with copy and pasting the text or some kind of formatting in the text. I copied the original message and pasted it in both Text Edit and Microsoft Word (and used Edit>Clear Formatting) and from there into a new Mail Message, attached the two files and it didn't send again. 

One attachment is a .jpg another is a .pdf. The total size of both is 104kb (well within our sending limit). The body of the message is 3-4 paragraphs, maybe 100-200 words total. I don't think it is a size issue.  

This could possibly be two issues, or just one: Mail just not sending attachments (even though it seems to have been corrected after removing the email account and adding it back), an issue with formatting that is somehow keeping Mail from sending attachments, or a mixture of both. 

On a side note, I added the same email account to another computer using 10.7.5 and added the correct imap and smtp info and the same issues and results happen with this specific email. (Other than this one email issue in 10.7.5 the only complaints about emails not sending attachments is coming from 10.9 users) 

I'm at a loss right now of what to try next. Since some of the iMacs have upgraded to 10.9, Apple Mail has been giving us some issues. 

Info:
iMac, OS X Mavericks (10.9.5), Apple Mail 7.3

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Info:
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