Problem sending large attachments using Mac Mail

[sadams@bigrocksports.com]

Release 7.1.0_GA_3140.RHEL5_64

Our Mac Mail users can no longer send out messages with attachments larger than around 1 MB. Webmail works fine. This started around the time we upgraded to 7 over a month ago. Our config is set up to allow up to 30 MB.

When sending via Mac Mail, the user gets a popup at the end that asks if they want to try another server. It acts like it is uploading the attachment and takes about as long as it should depending on the connection speed and size.

I have tried to sort through zimbra.log but it is massive and I am having a hard time determining if the attempt to send ever hits the logs.

Any help troubleshooting this is appreciated.

[joshmas]

I've been having the same issue where a Mac Mail user can send large attachments (20MB) through Webmail, but not through Mac Mail. He's receiving the same error as you. We're using an internal Exchange server with attachment limits up to 30MB. It's obviously related to Mac Mail. Would love to know if you find anything.

[sadams@bigrocksports.com]

It looks like the problem was with the milterd service.**

[root@webmail log]# grep 538E02D7A6C4 zimbra.log
Jun* 2 11:28:44 webmail postfix/smtpd[23728]: 538E02D7A6C4: client=rrcs-24-199-241-82.midsouth.biz.rr.com[24.199.241.82], sasl_method=PLAIN, sasl_username=sadams
Jun* 2 11:28:44 webmail postfix/cleanup[29320]: 538E02D7A6C4: message-id=<D54C655F-416E-4707-912A-E4A88278FD41@bigrocksports.com>
Jun* 2 11:31:49 webmail postfix/cleanup[29320]: 538E02D7A6C4: milter-reject: END-OF-MESSAGE from rrcs-24-199-241-82.midsouth.biz.rr.com[24.199.241.82]: 4.7.1 Service unavailable - try again later; from=<sadams@bigrocksports.com> to=<shannon_adams68@yahoo.com> proto=ESMTP helo=<[10.10.1.191]>

This details some of it:
Adjusting SMTP/milter timeout?

We had turned on the milterd service last month when we upgraded to 7. *For now, we just turned off the service and my test went out successfully.* We could probably tweak the time out settings for SMTP, but we will deal with that later.*

All my tests from Mac Mail work now that we turned off the milterd service.

[Cynamin]

Hi, I am not computer or mac savy so please bear with me.

I am having the same issue. I am trying to send 11 large emails of pictures. (i have tried pando but the recipients dont want pando) mac mail says it has to be smaller then 40mb. so all the emails are under 40mb. this is the thing, some have gone through and sent and others are forever in the outbox... why?

For instance i have sent a 32.6, 34.4, 33.6, 34.5, 18.9, and 33.9mb emails with pictures in them. but the other ones that are similar in size just wont send now. they are 33.6, 38.4mb..... you get my point.

I have also shut down my macbook, wait a while and restarted and they still wont send. During all this, 24hours now of trying, I have sent myself 'test' emails to ensure it is working fine... Im getting them. I get the same message as you do, server something. oh also i have my hotmail forwarded to my mac mail... it's all i use so the emails that worked went through from mac mail with my hotmail address.

These are family photos. I can't just send one and not all of them.
This is the forum with the questions/answers closest to mine.
If anyone can help I would appreciate it.

[phoenix]

Originally Posted by Cynamin

I am having the same issue. I am trying to send 11 large emails of pictures. (i have tried pando but the recipients dont want pando) mac mail says it has to be smaller then 40mb. so all the emails are under 40mb. this is the thing, some have gone through and sent and others are forever in the outbox... why?

For the simple reason that when an attachment is sent to through the mail server it is converted into another format for transmission and that causes a size increase in the region of 20-30% larger than the original file. Which Zimbra product and version are you using?