Exchange servers and Mavericks Mail

Hi guys,

I might have a solution for the Attachment-gate which so far is working.

It seems that when you set up an Exchange account, two SMTP records are stored. Below what I get when an email bounces: Two Exchange outgoing mail servers...

This is what the Sr. Apple Tech told me to do:

Go to Mail/Preferences/Accounts and select the Exchange account. In the Account Information tab click on 'Edit SMTP Server List...' under 'Outgoing Mail Server'.

In the new window you might see:

Exchange (Offline) which is similar to the one that shows up in above screesnhot. This the 2nd SMTP record but not the one that is needed and seems to cause the problem. He asked me to delete that one by selecting it and clicking the - (minus) button under the list.

I did that and tried some emails and so far that solved the problem for me...

Update: After 3 hours of sending emails with several attachments bigger than 200Kb still no issues...

Think Attachment-Gate is closed..

seems to work perfectly .... Great !

How are you connected to Exchange?...

I have an Exchange Web Services connection to Exchange 2010, and Mail doesn't show any SMTP server in my outgoing mail server list - yet I can talk to Exchange OK, apart from the issue of failing to send mails with large-ish attachments.

Hence this solution doesn't work for me.

I also tried an earlier suggestion of including my domain name with my user id (e.g. domain\userid) as the Exchange login credentials, but again that doesn't solve my problem...

Am still hoping that Apple comes thru with a resolution...

@davidkelly: not a specialist, but just follow the instructions and see if the screen shots match yours.

Thanks, but the screen shots do not match what I see on my system. I followed the instructions but I don't have any outgoing SMTP server for my Exchange account. If I go to Mail/Preferences/Accounts and select the Exchange account, then in the Account Information tab click on 'Edit SMTP Server List...' under 'Outgoing Mail Server', I only see the SMTP server for my ISP mail account (not my Exchange account that I use at work):

If I go to Mail/Preferences/Accounts and select the Exchange account, and "Account Information", then both the "Internal Server" and the "Outgoing Mail Server" are correctly identified as being the Exchange server. But clicking on "Edit SMTP Server List" under the "Outgoing Mail Server" drop-down list, only shows me the SMTP server for my ISP.

This sounds correct to me, as I understand that Exchange does not use SMTP for outgoing mail if the connection to Exchange is via Exchange Web Services.

Just a bit of background on attachment sizes.

Entourage EWS and Outlook for Mac use a new protocol called Exchange Web Services (EWS). Entourage 2008 and earlier use an older protocol called WebDAV.

The EWS protocol has a default limit of 10MB.

Your administrator needs to verify he's setting the limit for EWS to match the limit he's placed on MAPI. These two protocols are set independently of each other. 10 MB is the default limit for EWS.

http://technet.microsoft.com/en-us/library/hh529949.aspx

Whether this has any bearing on Mavericks Mail and Exchange issues is unclear.

This thread seems to have migrated from slow incoming mail to outgoing attachment problems.

In response to the original problem I agree with gjboz some pages back, Airmail is another alternative to Outlook2011 to get Exchange incoming emails moving again, the advantage over Mavericks Mail being it seems to prioritize newer mails.

I have bought Airmail myself and it out performs Mail even for IMAP, as fast as ipad mail.

Been using that tweak I described a few days ago for a few days... and sending emails with attachment >200K is causing a problem again... so only successful for a few days...

Apple... anybody out there???

The issue I had with Mavericks and Exchange Server 2003 is that Apple Mail stopped showing the subfolders in my inbox all of a sudden. It was working fine for about a month. Then even Outlook 2011 for Mac stopped syncing properly with my iPhone. When I deleted a message from the computer it didn't delete from the phone. If I deleted from the phone, it did delete from the computer.

Tech support told me that this is a known Exchange problem. I did a clean install back to the version before Mavericks and things are back to being right.

The bad news is very Likely the problem or a different problem will creep up on you in a fee days. The good news is that Apple is working on the problem and We finally got them to acknowledge the issue. All of these workarounds which I believe are not permanent will be superseded when they find the real issue and issue an update.

Mavericks and Mail has been my Windows Vista moment on Apple. That they were not able to fix the exhchange attachement and connectivity problems with the 10.9.1 update is disappointing.

My fix after 2 months of troubles: Moving back to Mountain Lion, everything is fine now.

stevenzac wrote:

The issue I had with Mavericks and Exchange Server 2003 is that Apple Mail stopped showing the subfolders in my inbox all of a sudden. <snip>

It was acknowledged early in the thread that having subfolders in your inbox would cause problems. An inbox is best as a pure inbox, rather than a filing system, even though it may have worked that way before Mavericks.

Having folders elswhere to categorise stored mails is fine.

Personally our family members have gone to Outlook 2011 and/or Airmail until the Exchange incoming delays are acknowledged and fixed by the Mail system designers.

I understand that but Apple should have let everyone know about this shortcoming before people upgraded to Mavericks. Surely there was enough beta testing with exchange server to find out about this problem. You should be able to use the inbox with sub folders. I have no problem using outlook for Mac but then it stopped syncing properly with my iPhone.

Are Beta testers typically business people running Exchange? Probably not. Do business people have time to complain on forums? Probably not. It is how it was missed and has been given low priority in my opinion.