Mail continuously fails with Exchange

I am running into a seemingly bizarre problem with Mail.

My work uses Exchange. I have things setup on my iPhone 4S and iPad 2 with no issues; however, I am just not able to get things setup properly using Mail on 10.9

If I let it auto discover, it takes ages and eventually fails asking something about whether I have SSL properly enabled.

If I enter in the info as seen on my iPad or iPhone, it then fails much more quickly with the message that "Trying to log in to this Exchange account failed. Verify that the username and password are correct."

The password is definitely correct and the username appears so. I even typed the password elsewhere, for the weblogin screen, and cut and paste it in - still gives this message.

Now on the iPad and iPhone it didn't have options for the port for SSL, you just toggle it on or off, so perhaps that is the issue here because it's asking for internal/external paths of EWS/Exchange.asmx

I don't know enough about this to know if that makes any difference, I just know I have the same data in the same fields and it doesn't appear to work at all. I've even used the IP, as suggested on my work's IT site, and it makes no difference.

My personal gmail account had no issues at all.

The internal and external server are the same: mail.domain.ie
username is set as what I login with. I've tried it as the both login and login@domain.ie neither does any good. I even tried it as domain\login and it gave the same error message. When I tried domain.ie\login it failed with a general error, so that wasn't correct

Under advanced I have SSL in both categories ticked. The internal port in both is 443 and they are both listed as EWS/Exchange.asmx and ews/exchange.asmx accordingly.

On my iPhone, it's set up as an Exchange and it the fields I have:
server: mail.domain.ie
domain: domain <-- no.ie on that one. Just the main bit.
username: login
password: password
Use SSL is ticked on.
Use Mime is ticked off.

Any suggestions are appreciated.

monkeybagel said:

You can try logging in with username@intdomain.inttld and see if It authenticates you. Most internal domains have a different domain name than used externally, so try entering the login in the form of windows.username@internaldomain.internaltld and leave "Domain" field empty.

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Thank you for your suggestion.

You say to leave the Domain field empty? Which field is that? I don't see a domain option in the Mail, but maybe I'm missing it in which case that be great, because I am hoping for an easy fix!

I may have not been clear, but it is the Mac that is having an issue - the iPhone/ipad, which has the domain option is actually working grand

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ScoobyMcDoo said:

What is the exchange server version? Just asking because the older versions don't play at all with Mail. My company just finally moved from a really old server to a much later version. It sort of works with Mail, but not very well. I eventually punted and used Outlook. I also tested AirMail which worked nicely also.

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Is there any way I can tell what the exchange server version is without any special access?

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MisterMe said:

ScobbyMcDoo is correct. Mail for OS X is compatible with Exchanger Server 2007 and later. Mail for iOS also works with earlier versions of Exchange Server. If you have even a thought about cursing Apple for this situation, then remind yourself that Exchange Server is proprietary Microsoft software. Microsoft's own Entourage 2004 and Entourage 2008 are the only two MacOS X-compatible communication clients that are compatible with Exchange Server pre-2007. However, Entourage 2004/Entourage 2008 is incompatible with Exchange Server 2007 and later. Microsoft replaced Entourage 2008 with Entourage EWS. In the next full release, Microsoft changed its name to Outlook 2011. Under whichever name, Entourage EWS/Outlook 2011 is incompatible with Exchange Server older than ES 2007.

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I definitely am not intending to curse apple and hope I didn't come across that way. I'm just having trouble and am frustrated because I've never had any real joy with Exchange. When I was in school, the Inns used exchange and it was equally as frustrating until they further enabled imap.

I just hope there's a way I can make this work.

satcomer said:

I found somethings on Google Search for you here.

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Thanks for that. I had seen most of those that come up at the top already. I also had googled my exact error message and the one previous. Nothing really seemed to apply, unless I'm missing something obvious, which is possible.

satcomer said:

Now please are you on their Domain or trying to get Exchange from outside the Domain? Plus do you know what version of Exchange it using?

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Outside of the domain.

Not sure how to tell what version of exchange is running. I logged on to the webmail portion, but nothing jumps out.

satcomer said:

Then give the forum he web site that your are getting the Exchange from and web page address (so we can look up the proper setup). Most web serves will have a setup page that the proper setup address. So do you have web site were that can be looked up?

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The proper setup information is probably behind the login I'm afraid, but I attached the images below. They don't have setup information for desktops, oddly just the iPhone.

satcomer said:

Plus in 10.9 you setup email account in System Preferences->Internet Accounts pane then highlight the Exchange Server string.

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Forgive me, I'm not sure what you mean by Exchange Server string.

When I go to the Internet Accounts pane, I see the Exchange icon. When I click it, in the pane to the right is a tick box by Mail. When I double click that, then I get all the setting information.

sliceoftoast said:

@ profchildermass everything you are experiencing i am also having problems with as well.

Mail not connecting to the exchange server, and when it does only the contents of the Inbox is displayed. It intermittently updates the inbox, i can see new emails come straight to my phone my Outlooking running in my Windows VM yet Mail will sit there and do nothing despite synchronising.

My Company is running Exchange 2010 and i did have these issues with 10.8.5

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I don't even get that much, as it consistently fails. Everything is setup fine on my iPad and iPhone and those are connecting to the Exchange without issue.

While I don't know for certain, I'm thinking it may be because the Exchange is a version not compatible, though that's just speculation given what people have said above. I'm hopeful that it's just I have something setup wrong, because it will be fiercely annoying if I can't access work emails on my laptop!

sliceoftoast said:

My iPhone / iPad basically any IOS device works fine NO problems at all It is just Mail that intermittently works.

I don't know if it is a Mail compatibility thing, or Exchange isn't configured properly. I know that in the past my mac has been connected to Exchange 2007 / 2010. Mac OS 10.7 - 10.9 and mail i don't think has every worked correctly.

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Has a different programme worked fine for you? I purchased AirMail and that didn't work for me neither.

hans1972 said:

Mail uses Exchange Web Services (EWS) to contact the Exchange-server. Most Exchange implementation do not configure and use EWS.
iOS uses ActiveSync to contact the Exchange-server. Most Exchange implementation do configure ActiveSync.

The only way to get Mail to sync with Exchange is to contact the Exchange administrators and ask if they can enable and configure EWS.

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Is there no other workaround? Does a mail programme on OSX use ActiveSync?

I will definitely contact them tomorrow, but I am worried they will just tell me to use the webmail. Thanks for telling me this bit, because at least I know what I can say.

mannyo1221 said:

Looking at the current login screen, the current server is running Exchange 2010.

The screen shots you have posted, the login screen for the web interface in these is exchange 2007, so you can see the difference.

So it should work fine with mail since the backend is not Exchange 2003 or earlier.

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Could the issue be, as someone else posted, that they don't have EWS configured?

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sliceoftoast said:

I haven't used Air mail.

I just put it in the can't be stuffed basket at the moment and i have just configured Mail to use our IMAP server instead of the exchange. NO problems so far, emails are updated instantly

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Ye, unfortunately for my situation we don't have an IMAP server or I would have long abandoned this!

petvas said:

As an Exchange consultant, I can tell you that this is something we don't like to do. IMAP and POP3 have different requirements than MAPI and most of the times Exchange Servers are being sized for MAPI and OWA only (and ActiveSync). IMAP and POP3 are also not really secure and Exchange admins don't want to enable the protocols.
Asking an Exchange admin to enable IMAP won't happen in any serious company.Maybe only in companies that are very small and don't have dedicated Exchange admins...

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You are correct, that isn't going to happen. Part of the reason I have to use this email is because of security concerns. I just really hate web mail. I hate how I don't get a notification and so forth, and I really dislike Outlook web mail.

petvas said:

As others have already stated, EWS has to be published on the Internet (EWS is always on but has to be made available on the Internet). EWS is also a requirement for Outlook Anywhere, so if you have colleagues with Outlook connecting to the Exchange Server through the Internet, then EWS should already be published. Normally autodiscover would find the settings by itself, unless of course Exchange is not accordingly configured. You mentioned the certificate also. Maybe your company doesn't use a trusted certificate. There could be many reasons...

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Thank you for this information.

I went into the IT department today and it was a bit of a frustrating farce. They said the direction of the world is to just use webmail and said I should be happy with that. That you can see the direction with gmail. I thought the explanation was a bit poor, since gmail has imap and that now even hotmail has added that, so it seemed a bit inadequate. This administrator also said that "now that Microsoft finds Apple to be competition, it stopped working." Apparently it used to work and then they updated and it hasn't worked since. They told me they had several consultants come in and no one could get it to work and that they have a query pending with Microsoft for quite some time now. They told me there's no consultants that are experts in Mac in Ireland, though I'm not certain how true that was.

Interestingly they said it will work if I use windows and they also said it will work on a mac if I am on the network.

I am going to go to one of the Bar Council representatives tomorrow, because the three IT admins I had a meeting with today brushed me off.

Does the fact that it will work when "in network" mean their EWS isn't configured properly?

When we talk about how it needs to be published, is that relevant to the section on Mail where I add an Internal server path which is EWS/Exchange.asmx and a separate option of External server path? How involved is setting up something like this? Am I really asking for something considerable or is this something that a knowledgable admin could do without too much time? Finally, I know a couple of my colleagues would be on a windows laptop and likely use Outlook...is it a matter of copying what they have for Internal server path, etc?

Appreciate your help on this, I'm very grateful.

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sliceoftoast said:

Microsoft Exchange Servers Support IMAP / POP3 / Exchange. Just tell your IT admins to turn on the iMAP service, enable it on your user account. Is there a company policy to all use exchange accounts?

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I mentioned this and they said something about security and clouds. I didn't take notes on that part. It's not really a company policy to use exchange, as it isn't exactly a company, but I imagine if I used client sensitive work on my gmail and my gmail was compromised I would have some liability - whereas, I would not have personal liability if this email was compromised.

petvas said:

The administrator's answer is plain ridiculous.
In order to make Exchange work with Mac from the Internet you need the following things:

• The externalURL value on the Exchange CAS Servers has to be configured with the url of the published servers.
• The CAS Servers should be published (by using a reverse Proxy like TMG or an equivalent application firewall) to the internet
• The publishing platform has to use a valid public certificate, pointing to the name, as configured in the ExternalURL property of all CAS Servers.
• The EWS virtual directory should be configured with basir or/and Windows authentication.
• Autodiscover has to be properly published. It is always autodiscover.smtp.domain of the company. This name should point to the publishing platform, which in turn publishes the Exchange CAS Servers
  

I have hundred of customers and I have configured many Exchange Servers and had zero issues with Mac Mail.
This is easy stuff for any Exchange consultant!

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Thank you, that is very helpful. I hope I can succeed at convincing them to make the bother.