I can't send messages with attachments using my Apple Mail account

Question

Level 1

4 points

I can't send messages with attachments using my Apple Mail account

Hi,

I have a problem with my Apple Mail account. About a month ago it suddenly stopped allowing me to send messages with atachments (although sending messages with JPEGS attached are okay). I can send messages without attachments and receive messages with attachments. However, messages with attachments appear to have been sent as they appear in my 'Sent' folder so it's all a bit confusing. I'm sure it's not a problem with my ISP as I can send okay using hotmail, gmail etc. I also have nearly 3 Gb of storage available so that can't be the problem. I'm using a MacBook Pro3,1 (a few years old now) and I'm using Mail version 4.6 on OS X 10.6.8. I have turned off/restarted my router and quit Mail and reopened the application but all my efforts have proved unsuccessful. Can anyone please help?

Thank you,

Nick

MacBook Pro, Mac OS X (10.6.8)

Posted on May 22, 2015 6:23 AM

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Answer 1

Eric Root

Level 10

684,027 points

May 22, 2015 6:32 AM in response to Nick-OS X 5

If the messages appear in the sent folder, how do you know they weren't sent? How large are the attachments you are trying to send since some ISPs limit attachments size? What file format won't send since you posted JPEG attachments would send? Have you tried control - clicking the attachment and selecting compress?

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Answer 2

Nick-OS X 5 Author

Level 1

4 points

May 22, 2015 6:55 AM in response to Eric Root

Hi Eric and thank you for your reply. It's not a ISP content restriction as I have sent the same attachments (yesterday) using my gmail and hotmail accounts. As I said, the emails appeared in my Mail's Sent folder so I thought they had been sent and only realised that there was a problem when intended recipients told me they had not received my emails. I then forwarded them to my gmail/hotmail account and, again, though logged in my Sent file they didn't appear in my gmail Inbox. I've been using Apple Mail for my mac,com emails for around 8 years and this is the first time I have encountered this problem. Regards, Nick

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Answer 3

Nick-OS X 5 Author

Level 1

4 points

May 22, 2015 6:56 AM in response to Eric Root

You also asked about the file formats. Word, Excel and PDFs mainly.

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Answer 4

Eric Root

Level 10

684,027 points

May 22, 2015 8:20 AM in response to Nick-OS X 5

You are welcome. Did you try control - clicking them and selecting compress? What happens if you send the e-mail with attachments to yourself?

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Answer 5

Nick-OS X 5 Author

Level 1

4 points

May 22, 2015 8:32 AM in response to Eric Root

Hi again Eric. I tried this as well and can only send messages without attachments to myself although all go into my Sent folder. I haven't tried to compress data as, until recently, I was able to send several uncompressed attachments in the same email. It just seems as though a glitch has appeared and no amount of fiddling will clear it. Someone suggested removing and then restoring my Mail application but I'm not sure how to do this.

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Answer 6

Eric Root

Level 10

684,027 points

May 23, 2015 8:16 AM in response to Nick-OS X 5

You would have to reinstall the OS to get a new copy of Mail.

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Answer 7

Camelot

Level 9

54,333 points

May 24, 2015 1:44 AM in response to Nick-OS X 5

It's not a ISP content restriction as I have sent the same attachments (yesterday) using my gmail and hotmail accounts

Unfortunately, that's a completely irrelevant basis and, indeed, I think points you towards the problem.

Let's say you have three email accounts configured, one for your ISP-based account (or maybe for your own domain if you have one), one for Gmail and one for Hotmail.

When you send an email from Gmail, your client sends the message to Google, who then forward the message to the recipient.

When you send an email from Hotmail, your client sends the message to Microsoft, who then forward the message to the recipient.

When you send mail through your own/ISP account, your client sends the message to your ISP who then forwards it.

Do you see the difference? for each account, it's going through completely different servers, each of which could have their own settings for content filtering.

In addition to that, if you're running your own domain it's possible that you don't have the anti-spam configuration setup properly, so it could be getting through your server (which is why its in your Sent Items folder), but it's being rejected by the recipient mail server because it looks like spam.

Without more detail, it's hard to be more specific, but I'll go out on a limb and say it's got nothing to do with Mail.app itself, just the configuration of your mail accounts/servers.

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Answer 8

Nick-OS X 5 Author

Level 1

4 points

May 26, 2015 1:09 AM in response to Camelot

Hello Camelot.

I appreciate your efforts to explain the weaknesses in my theory. I have to admit that I do not presume to have any useful insights into this; it just struck me as odd that I suddenly was unable send an email with an attachment and that hitherto I had never experienced this problem. I don't have a domain; just an Apple email address operated through my Mail application. The regular recipients of my attachments haven't changed the settings on their email accounts or their ISP so it seems inexplicable that my messages are now being diverted as spam. If it is the case that the configuration of my mail accounts/servers has changed is it owing to something I might have done inadvertently and what can I do to troubleshoot and effect a cure. Any further guidance would be greatly appreciated.

Thank you again for your help.

Regards, Nick

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