Mavericks Mac Mail Can Not Connect To Server Intermittantly And Mail Stays In On My Mac In Outbox For Ages Instead Of Going Into My Exchange Account

I have the exactly the same issue here and have been experiencing it for a month or two. The OSX upgrade just made everything worse. It's actually good to know I'm not the only one contemplating throwing my shiney new MacBook Air at the window...

Gmail accounts work fine. Exchange however works, stops working, works, stops working, etc, etc, etc.. It can be fine for 2-3 hours and then suddenly I get all the usual messages saying it can't connect to the Exchange Server, I click try again, and it either stays there in the Outbox for years, or will somehow connect through. Have checked everything - all running ok, SMTP settings all correct, the Mac connects through to the server when tested, and yet I keep getting this REALLY ANNOYING problem which means I can't send or receive business emails at exactly the time when I need them, or I end up sending the same email 6 times becase I've clicked try later about...6 times in frustration.

FOR THE SAKE OF MY SANITY, SOMEONE IN APPLE READ THIS CHAIN AND DO SOMETHING. PLEASE. How do we solve this problem. I cannot believe the answer is to ditch Apple and go back to MS Office. Surely not!?!?!?!

Adam

Guess its good there's a fix coming but for business reasons I've already switched to Outlook for Mac. Not sure I'll switch back now. Since AAPL doesn't provide guidance on problems/solutions/timing, I don't see how they can be relied on for mission-critical functionality.

warypb1 wrote:

YOUR JOKING ? Seriously, most of us have just upgraded exchange servers to 2007/2010 due to the incompatability with Exchange and Mac Mail.

Now they are saying that MAC mail doesnt work in an Exchange enviorment - Apple please confirm if your out there!

I use Mac Mail and Exchange 2007 as well as 2013, it works fine.

I had this issue for a while and it was very frustrating. I have a few exchange accounts on the same server, and one was working while the other was intermittant. What I discovered is that the working on had the full UPN (name@domain.tld) and the intermittant one had just the name specified. My email server has a default domain set for EWS, but for some reason with Apple Mail in Mavericks just using the name (and relying on the default domain) was intermittant. Recreating the account using the full UPN seems to have fixed the problem. I'd suggest you give that a try and see what happens.

I've got Outlook 2011, and am use GoDaddy email and I've been seeing the same intermittient mail send failures since upgrading to Mavericks. I've got Outlook setup for 4 different email domains. SInce the upgrade sometimes 5 or 6 times a day, the same error. I've been using these same email accounts for over 5 years.

"Outlook cannot find the server. Verify the server information is entered correctly in the Account Settings, and that your DNS settings in the Network pane of System Preferences are correct." Error code: -3170

Some of the smtp ports use SSL other dont. This has got to be some sort of Mavericks network or port issue.

I've just started having the problem of replies to emails being stuck in the Outbox. I went to Window > Connection Doctor, and found that the SMTP Account Type had a red dot with details showing connection failed. I double-clicked on the SMTP line, and an Accounts window popped up. I reentered the password and clicked OK. The red dot turned to green, and Details showed "Connection and login to server succeded". Emails are now going out, and fingers crossed everything seems to be working.

I have similar issue with Mail on Mavericks. I don't think it's an issue with the new OS nor the latest update. Ever since i log in my gmail account on an andorid device my mac mail stopped connecting to all the accounts on my mac mail. Including my school mail account, iCloud, Gmail. When i open up the connection doctor under window in Mac mail. All the SMTP and IMAP account was offline. I could not even run any network diagnosis in that window... It might be an coincident of this misfortune occur after signing in to an android device.

Users at my company are experiencing the same sending issue. We are running Exchange 2007 and the 6 or so users who've updated to Mavericks are all experiencing the intermittent send issue. We have 80 or so total users most of which are still on 10.8 and have no problem sending email through Apple Mail. A couple of the Mavericks users have switched to Outlook 2011 and have no issues either, it's just those running Mavericks and Apple Mail that have the intermittent problem. Accounts have been deleted and recreated in Apple Mail but the problem still continues.

Thanks BravermanA, it works for me, I couldn't connect to the server in our school. I used only name. Actually we should use win/123456 as the name when log on to outlook. But I use my whole email address like xyz@abcd.edu (instead of just xyz or win/123456). You can use autodiscover. It works now. I can login and Mail.app start to fetch mails now.

Howevery I am still testing sending email.

It stop working again. So this is not a very successful way. BravermanA, could you explain more clear how to setup the mail for exchange.

BravermanA - that sounds promising. Could you spell out an idiots guide as to how to check and then do what you did? Thank you! Adam

Akamaxpower, your 80 ML users should stay there. If there is any evidence that your Exchange implementation will not work smoothly then until the cause is found, any upgraders will need Outlook2011 or Airmail app for $1.99 which works well

Not all exchange users have these problems, but you yourself are now stuck with it, and if you have Outlook 2011 you would do well to switch.

Short:

Use the external IP address, force it into all instances of the connection - Mail, Contacts, Calendars, Notes, and Reminders. If your external mail server is populated in the preferences box - from OUTSIDE your corporation, use the command $ nslookup {mail.server.address} to find the IP address, then use that IP Address in all the boxes. Save the account info, exit the apps, restart your Mac. You should be good from then on.

Long:

I had the same problem and worked through my difficulties and have a solution.

Also, I believe the problem is with Internet Accounts - common information between Mail, Contacts, Calendars, Notes, and Reminders.

For me, I could force the problem to reproduce by VPNing into my corporate network, then disconnecting the VPN - minutes or hours later, didn't matter. While the transition into the corporate network went fine, it appears to get stuck trying to use the Internal name/IP even after disconnecting. It would not "release" this lock until I rebooted. I even tried the whole tech support 45 minute phone call, add a "take offline / online" Toolbar Shortcut, etc - none of it worked until I rebooted each time.

Now I believe you could resolve it by resetting the network connection ($ sudo ifconfig en0 down / $sudo ifconfig en0 up), but I resolved my issue before testing that out. And who wants to reset the network connections everytime this problem comes up?

I discovered my Internal and External server boxes were inconsistently populated, and decided to manually populate all of them (turn off autodisover) with the IP Address of the external server, so it would always work whether inside or outside the company network.

Preferences (Command ,) then Accounts, select your exchange account in question:

Account Information tab - un-check the Autodiscover service, manually enter the IP of the external server in both Internal Server and External Server boxes.

Advanced tab - make sure your Internal Paths and Ports are manually configured properly (with or without SSL as needed by your mail server).

Save the settings (change accounts or close preferences and save).

You may be prompted with a warning - the SSL Certificate does not match. This is because your "*.company.com" SSL Certificate does not match the xxx.xxx.xxx.xxx IP Address you entered - which is understandable. Just verify the certificate is for your company's domain, and Accept (Trust) it permanently - which will require you to provide admin credentials to save the certificate settings.

Good morning,

I can confirm that this method works for me and I've used it on machines inside a corporate network and external to the corporate network.

They key is in fact making sure the Calendar preferences, Contacts preferences and Mail preferences have the same settings - exactly.

On the inside-corporate netowrk, I had to backup and move the ~/Library/Mail folder as it was still named using an old domain name that was (maybe) confusing things. This works for exchange and IMAP, but careful if you are doing this for POP, (needless to say - have a backup in place).

I still have difficulties sending occasionally from outside the corporate network, and I had thought of using the fixed IP in the 'External Server' box... and I'm going to try it now that you mention it.

Will update and let you know what I find. Thank you for the comprehensive write-up.

Peter