Microsoft Exchange Server on Mac OS X Server

I am running Mac OS X Leopard Server on my Mac Pro with multiple clients, all using Mac OS X Leopard. Each client also has Microsoft Office 2008 for Mac installed with Entourage. Is it possible to install Microsoft Exchange Server on the Mac Pro and use it to set up calendaring for all of my Mac clients through Entourage?

Hi Benjamin,
Apologies for Jeff's rather useless answer.
You can absolutely install Microsoft Exchange on a Mac Pro server to accompany OS X Server.
Head over to VMware, Parallels or Oracle and grab a virtualisation hypervisor. I personally recommend VMware ESXi.
Setup a Virtual Machine running a copy of Microsoft Windows Server 2012 and Microsoft Exchange Server 2013. (More information here http://www.microsoft.com/en-us/server-cloud/products/windows-server-2012-r2/buy.aspx#fbid=f4pyYTvvgji and here http://office.microsoft.com/en-us/exchange/microsoft-exchange-server-2013-business-email-email-server-try-now-FX103765014.aspx)
If you would rather not involve yourself with all the fuss involved with maintaining Microsoft Exchange, head over to Microsoft Office's website and Subscribe to Office 365 for Business. If you would rather not work with Microsoft at all, head over to Google
and setup Google Apps.
Thanks,
Will

Similar Messages

Microsoft Exchange Account on Mac OS X Lion latest version

- I successfully add my company microsoft exhange account on my iPad2 and iPhone4S.
- I tried to add on my macbookair via "system preferences" / "Mail Contacts & Calenders" but on Mail on Calendar and on Address Book i get the same message type of error witch consists on a "server not reponding" on port XXX ...
- Is there a different aproach when add a microsoft account on iOS (iphone/ipad) and on OS X Lion (macbookair)?
- Does apple have a step by step guide to add a microsoft account on Lion?
Thank You,
Paulo.

Hi Benjamin,
Apologies for Jeff's rather useless answer.
You can absolutely install Microsoft Exchange on a Mac Pro server to accompany OS X Server.
Head over to VMware, Parallels or Oracle and grab a virtualisation hypervisor. I personally recommend VMware ESXi.
Setup a Virtual Machine running a copy of Microsoft Windows Server 2012 and Microsoft Exchange Server 2013. (More information here http://www.microsoft.com/en-us/server-cloud/products/windows-server-2012-r2/buy.aspx#fbid=f4pyYTvvgji and here http://office.microsoft.com/en-us/exchange/microsoft-exchange-server-2013-business-email-email-server-try-now-FX103765014.aspx)
If you would rather not involve yourself with all the fuss involved with maintaining Microsoft Exchange, head over to Microsoft Office's website and Subscribe to Office 365 for Business. If you would rather not work with Microsoft at all, head over to Google
and setup Google Apps.
Thanks,
Will

The server at Mac OS X Server Web Services requires a username and password

I am running SL Server 10.6.2, wiki works but when a person clicks an attached file in a wiki and then selects "open" they get a login popup with the notification The server at Mac OS X Server Web Services requires a username and password. It doesn't matter what they put into the login/pass it comes back. If they hit cancel then the document opens. If they click save then it saves with no issue. I can type in the admin login/pass of the server and it works. Does this mean the security settings to the location of the files is wrong? Any help is greatly appreciated!

By the way they are using Internet Explorer 7 when opening these documents.

Push-Technology Support for Exchange - and for Mac OS X Server - users?

To have support and compatibility for using push-email, -calendaring and -address books updating with Microsoft Exchange Server 2007 is very much appreciated. But how about small enterprises who so far relied in Leopard Server and seek for similar push technologies in conjunction with the iPhone? I am not a professional but can push-email, -calendaring and -address books updating with the current state of Leopard Server? If not, does Apple plan to integrate a solution? If yes, when?

We're all just your fellow users here and have no insight into Apple's future plans. You can submit your comment and suggestion to Apple through their feedback pages:
http://www.apple.com/feedback/

RADIUS Server on Mac OS X Server 10.5 Leopard

I must set up a Radius Server on my LAN and WLAN, I will do this with Mac OS X Server v.10.5 Leopard but I don't know if it's compatible with any routers(for LAN and WLAN Access) and with Windows XP Pro SP3 computers.
Can anyone help me????

I know this question is fairly old but I can now state that as of last night I am using a Netgear WN802T - 200 access point paired with the RADIUS service on a Leopard Server.
Leave the "type" of station either blank or other for Netgear.
Accounting does not seem to work and throws errors in the radiusd log, but other than that the Mac clients and iPhones show a WPA2 Enterprise connection.
Your mileage may vary.

Exchange alternative for Mac Snow Leopard Server

I was wondering what are some good alternatives to Microsoft's Exchange service for use in the new Snow Leopard Server that will be coming out. I am aware that Snow Leopard Server offers open source for mail server, but I would like to go with an actual GUI interface with a third party software. Any suggestions would be great!

You will not be able to do any extensive management of Active Directory from with Mac OS X natively,
and considering the technology, it's best managed using the native Microsoft tools & technologies anyway. There are products that offer options for Mac management from/via AD - beyond what Apple provides and/or is possible by extending your schema, but that's _another matter entirely_.
"Closest thing" is really for you to decide, you will need to investigate the products and if they will meet your needs.
As I have stated, what we know will be available in & via Snow Leopard is what Apple has made known on its own preview pages.
If you needed to seriously know more you would have invested in a ADC Developer account and extensive testing but with the understanding you would be dealing with pre-release technology.
Past that, the two products that offer the most in terms of feature-set(s) are as I already noted:
Kerio
and
Zimbra.
Best of luck !

Run HTTP File Server on Mac OSX Lion Server?

Hello!
I have a Mac Mini running Mac OS X Lion Server.
I would like to be able to host a Web Server that runs within the built in Apache server that allows the transfer of files from Client to Mac Mini HD and vice versa using authentication from Open Directory.
My inspiration is HTTP File Server, or HFS (no, not the Disk Format). This, however, is a Windows Program. It allows a HTTP platform to upload and download files from the HD of the machine it is running from. It comes as a nifty .exe that has everything you need. I'd like something similar but to run on the Mac Server.
Note, the upload and download cannot be done over FTP. It must be using HTTP like HFS does.
At the very least, I'd like a HTTP (Port 80) Web Server that runs within Apache that allows upload and download to the HD.
And at best, authentication using the built in Open Directory credentials. And to make even more secure, HTTPS or SSL.
So it's like iCloud or iWork.com but using my own disk space and credentials.
Predicted End Product:
User visits https://192.168.x.x or https://MyDNSName.dns.com
Greeted with Home Screen (.html or .php)
Clicks login
Has a nice login window to use (probably have to be .php to keep simple)
Logs in using same credentials as they would to logon to Mac Mini locally
Greeted with view of their files in their Directory, e.g.: /Library/Server/Web/HFS/User1 or /Library/Server/Web/HFS/User2, etc
Can choose to download present files
Or upload. Click Upload
Upload window appears. Selects file on Client machine.
Over HTTP, file is uploaded to Host Machine to /Library/Server/Web/HFS/User1
What I'd like to know is what is the easiest way of going about this? Some kind of CMS like Wordpress or software like HFS?
Many thanks,
Clark

I'm a little confused here... what's the requirement for HTTP based transfers vs. traditional file sharing protocols such as AFP?
Secondly, how does 'HFS' differ from any other HTTP form-based uploader? Any web CGI or scripting system such as PHP or Perl could easily present an upload form.
Have you considered WebDAV, which is designed as s file transfer protocol over HTTP?
It integrates at the Finder level, meaning you can copy files by simply dragging and dropping file (and folder) icons in the desktop, just like on a local drive. It's part of the standard Mac OS X Apache installation, too.

Internet Content Filtering Server for Mac OS X Server?

Hello everyone,
I was wondering if anyone knew of a product that would allow my LAN to have Internet Filtering. It would be really good if I could set up my Mac OS 10.4 server as a gateway that will allow users access to the web with a username and password. It would also be good if I could have guest access of restricted access that would only allow certain websites to work.
I guess I am looking for some form of proxy server?
Any ideas anyone?
Thanks,
David

I use Firefox, becasue I never put in the time to learn how Safari controls temporary/permanent cookie storage.
Firefox also has a large selection of add-ons to prevent javascript running or "tracking links" inside web pages, etc.

Issues with outgoing server - not mac or me server

dear apple list
i am having issues with outgoing mail server for my domain dot com email account
there error message reads:
The sender address x was rejected by the server smtp.x.org.
I contacted the hosting provider and everything is alright on their end. This problem just suddenly sprouted up - any suggestions? I changed the outgoing mail server from port 25 to 587 but to no avail.
Thanks

Hello NgaireClare,
Thanks for using Apple Support Communities.
Take a look at the following article to help troubleshoot the issue with your outgoing mail server.
OS X Mail: Troubleshooting sending and receiving email messages
http://support.apple.com/kb/TS3276
Take care,
Alex H.

Microsoft Exchange Server 2013 Cumulative Update 7 Setup - Active Directory Topology service on server 'TopologyClientTcpEndpoint (localhost)' returned an error - Set-SharedConfigDC

What am I trying to do?
I have tried installing Microsoft Exchange Server 2013 Cumulative Update 7 Setup on a fresh install of Windows Server 2012 R2 but it gets stuck when running the setup exe on Step 8 of 14 “Mailbox Transport Service” I have included full
error logs at the bottom of the page but the basics are in order it will throw which loop around are:
[01/20/2015 17:13:20.0084] [2] Beginning processing Set-SharedConfigDC
[01/20/2015 17:13:20.0178] [2] The call to Microsoft Exchange Active Directory Topology service on server 'TopologyClientTcpEndpoint (localhost)' returned an error. Error details No Minimal Required Number of Suitable Directory Servers
Found in Forest mydomain.com Site Default-First-Site and connected Sites..
[01/20/2015 17:13:20.0178] [2] No Minimal Required Number of Suitable Directory Servers Found in Forest mydomain.com Site Default-First-Site and connected Sites.
Exchange is currently running in the envirmonet on 2010 Sp3 I am installing 2013 CU7 fresh so I can migrate the databases over.
What am I running?
2 X DC on domain and forest functional level 2008R2 both writable
1 X fresh install of Windows 2012 R2 which is domain joined
What have I tried?
Checked Ipv6 is enabled on all DC NICS and Existing Exchange Servers
Rebooted every server
Run setup as Administrator
My account is part of the domain Enterprise Admin group
Tried adding "Exchange Server" or "Exchange Enterprise Servers" to the group policy and doing the relevant gpupdate /force and reboot :
Computer Configuration Windows Settings
Security Settings + Local Policies
User Rights Assignment Mange auditing and security log
Turned off firewall on DC and Exchange Server even stopped the service
Turned off all AV on the DC and Exchange Server
Checked I could telnet to global catalog servers on port 3268 which I can
Checked the global catalog records existed in DNS which they all do
Done the obvious ping tests all round which confirms connectivity
Schema has been prepared using appropriate commands before running the setup exe
setup.exe /PrepareSchema /IacceptExchangeServerLicenseTerms
Making sure the following path has full permissions:
EXCHANGE14:\Current\Release\Shared\Datacenter\Setup
Restarted Microsoft Exchange Active Directory Topology service
DcDiag all looks good
What have I noticed that is suspicious?
Microsoft Exchange Transport service will not start even though both of its dependences services have started:
Microsoft Filtering Management Service
Microsoft Exchange Active Directory Topology Service
It will eventually error with
“Windows could not start the Microsoft Exchange Transport Service on local computer
Error 1053: This Service did not respond to the start of control request in a timely fashion”
This error is from the GUI wizard itself:
Error:
The following error was generated when "$error.Clear();
$maxWait = New-TimeSpan -Minutes 8
$timeout = Get-Date;
$timeout = $timeout.Add($maxWait);
$currTime = Get-Date;
$successfullySetConfigDC = $false;
while($currTime -le $timeout)
$setSharedCDCErrors = @();
try
Set-SharedConfigDC -DomainController $RoleDomainController -ErrorVariable setSharedCDCErrors -ErrorAction SilentlyContinue;
$successfullySetConfigDC = ($setSharedCDCErrors.Count -eq 0);
if($successfullySetConfigDC)
break;
Write-ExchangeSetupLog -Info ("An error ocurred while setting shared config DC. Error: " + $setSharedCDCErrors[0]);
catch
Write-ExchangeSetupLog -Info ("An exception ocurred while setting shared config DC. Exception: " + $_.Exception.Message);
Write-ExchangeSetupLog -Info ("Waiting 30 seconds before attempting again.");
Start-Sleep -Seconds 30;
$currTime = Get-Date;
if( -not $successfullySetConfigDC)
Write-ExchangeSetupLog -Error "Unable to set shared config DC.";
" was run: "System.Exception: Unable to set shared config DC.
at Microsoft.Exchange.Configuration.Tasks.Task.WriteError(Exception exception, ErrorCategory category, Object target, Boolean reThrow, String helpUrl)
at Microsoft.Exchange.Configuration.Tasks.Task.WriteError(Exception exception, ErrorCategory category, Object target)
at Microsoft.Exchange.Management.Deployment.WriteExchangeSetupLog.InternalProcessRecord()
at Microsoft.Exchange.Configuration.Tasks.Task.<ProcessRecord>b__b()
at Microsoft.Exchange.Configuration.Tasks.Task.InvokeRetryableFunc(String funcName, Action func, Boolean terminatePipelineIfFailed)".
Exchange logs which have been written:
**The error will loop around for 8 minutes on trying to set-sharedconfig DC whatever this is trying to do ??
[01/20/2015 17:13:20.0084] [2] Active Directory session settings for 'Set-SharedConfigDC' are: View Entire Forest: 'True', Configuration Domain Controller:mydomain.com', Preferred Global Catalog: 'mydomain.com', Preferred Domain Controllers:
'{ mydomain.com}'
[01/20/2015 17:13:20.0084] [2] User specified parameters:
-DomainController:mydomain.com' -ErrorVariable:'setSharedCDCErrors' -ErrorAction:'SilentlyContinue'
[01/20/2015 17:13:20.0084] [2] Beginning processing Set-SharedConfigDC
[01/20/2015 17:13:20.0178] [2] The call to Microsoft Exchange Active Directory Topology service on server 'TopologyClientTcpEndpoint (localhost)' returned an error. Error details No Minimal Required Number of Suitable Directory Servers
Found in Forest mydomain.com Site Default-First-Site and connected Sites..
[01/20/2015 17:13:20.0178] [2] No Minimal Required Number of Suitable Directory Servers Found in Forest mydomain.com Site Default-First-Site and connected Sites.
[01/20/2015 17:13:20.0178] [2] The call to Microsoft Exchange Active Directory Topology service on server 'TopologyClientTcpEndpoint (localhost)' returned an error. Error details No Minimal Required Number of Suitable Directory Servers
Found in Forest mydomain.com Site Default-First-Site and connected Sites..
[01/20/2015 17:13:20.0178] [2] No Minimal Required Number of Suitable Directory Servers Found in Forest mydomain.com Site Default-First-Site and connected Sites.
[01/20/2015 17:13:20.0178] [2] Ending processing Set-SharedConfigDC
[01/20/2015 17:13:20.0193] [2] Beginning processing Write-ExchangeSetupLog
[01/20/2015 17:13:20.0193] [2] An error ocurred while setting shared config DC. Error: The call to Microsoft Exchange Active Directory Topology service on server 'TopologyClientTcpEndpoint (localhost)' returned an error. Error details
No Minimal Required Number of Suitable Directory Servers Found in Forest mydomain.com Site Default-First-Site and connected Sites..
[01/20/2015 17:13:20.0193] [2] Ending processing Write-ExchangeSetupLog
[01/20/2015 17:13:20.0193] [2] Beginning processing Write-ExchangeSetupLog
[01/20/2015 17:13:20.0193] [2] Waiting 30 seconds before attempting again.
[01/20/2015 17:13:20.0193] [2] Ending processing Write-ExchangeSetupLog
[01/20/2015 17:13:50.0195] [2] Beginning processing Write-ExchangeSetupLog
[01/20/2015 17:13:50.0273] [2] [ERROR] Unable to set shared config DC.
[01/20/2015 17:13:50.0273] [2] [ERROR] Unable to set shared config DC.
[01/20/2015 17:13:50.0288] [2] Ending processing Write-ExchangeSetupLog
[01/20/2015 17:13:50.0288] [1] The following 1 error(s) occurred during task execution:
[01/20/2015 17:13:50.0288] [1] 0. ErrorRecord: Unable to set shared config DC.
[01/20/2015 17:13:50.0288] [1] 0. ErrorRecord: System.Exception: Unable to set shared config DC.
   at Microsoft.Exchange.Configuration.Tasks.Task.WriteError(Exception exception, ErrorCategory category, Object target, Boolean reThrow, String helpUrl)
   at Microsoft.Exchange.Configuration.Tasks.Task.WriteError(Exception exception, ErrorCategory category, Object target)
   at Microsoft.Exchange.Management.Deployment.WriteExchangeSetupLog.InternalProcessRecord()
   at Microsoft.Exchange.Configuration.Tasks.Task.<ProcessRecord>b__b()
   at Microsoft.Exchange.Configuration.Tasks.Task.InvokeRetryableFunc(String funcName, Action func, Boolean terminatePipelineIfFailed)
[01/20/2015 17:13:50.0288] [1] [ERROR] The following error was generated when "$error.Clear();
$maxWait = New-TimeSpan -Minutes 8
$timeout = Get-Date;
$timeout = $timeout.Add($maxWait);
$currTime = Get-Date;
$successfullySetConfigDC = $false;
while($currTime -le $timeout)
$setSharedCDCErrors = @();
try
Set-SharedConfigDC -DomainController $RoleDomainController -ErrorVariable setSharedCDCErrors -ErrorAction SilentlyContinue;
$successfullySetConfigDC = ($setSharedCDCErrors.Count -eq 0);
if($successfullySetConfigDC)
break;
Write-ExchangeSetupLog -Info ("An error ocurred while setting shared config DC. Error: " + $setSharedCDCErrors[0]);
catch
Write-ExchangeSetupLog -Info ("An exception ocurred while setting shared config DC. Exception: " + $_.Exception.Message);
Write-ExchangeSetupLog -Info ("Waiting 30 seconds before attempting again.");
Start-Sleep -Seconds 30;
$currTime = Get-Date;
if( -not $successfullySetConfigDC)
Write-ExchangeSetupLog -Error "Unable to set shared config DC.";
        " was run: "System.Exception: Unable to set shared config DC.
   at Microsoft.Exchange.Configuration.Tasks.Task.WriteError(Exception exception, ErrorCategory category, Object target, Boolean reThrow, String helpUrl)
   at Microsoft.Exchange.Configuration.Tasks.Task.WriteError(Exception exception, ErrorCategory category, Object target)
   at Microsoft.Exchange.Management.Deployment.WriteExchangeSetupLog.InternalProcessRecord()
   at Microsoft.Exchange.Configuration.Tasks.Task.<ProcessRecord>b__b()
   at Microsoft.Exchange.Configuration.Tasks.Task.InvokeRetryableFunc(String funcName, Action func, Boolean terminatePipelineIfFailed)".
[01/20/2015 17:13:50.0288] [1] [ERROR] Unable to set shared config DC.
[01/20/2015 17:13:50.0288] [1] [ERROR-REFERENCE] Id=AllADRolesCommonServiceControl___ee47ab1c06fb47919398e2e95ed99c6c Component=EXCHANGE14:\Current\Release\Shared\Datacenter\Setup
[01/20/2015 17:13:50.0288] [1] Setup is stopping now because of one or more critical errors.
[01/20/2015 17:13:50.0288] [1] Finished executing component tasks.
[01/20/2015 17:13:50.0304] [1] Ending processing Install-BridgeheadRole
Windows Event Viewer:
Process Microsoft.Exchange.Directory.TopologyService.exe (PID=5276) Forest mydomain.com. Exchange Active Directory Provider couldn't find minimal required number of suitable Global Catalog servers
in either the local site 'Default-First-Site' or the following sites:

Hi apl228,
1. Please make sure the IPv6 is enabled.
2. Please make sure the account that install Exchange server has Administrator permission.
3. Please make sure DNS has been configured correctly.
Thanks
Mavis Huang
TechNet Community Support

Old Web Server Software on Mac OS X Server 10.4.6?

I am wondering why my apache that is running is only 1.3.33 accordign to my webmin tool that my friend installed, the php and sql are old too.
I'm not a unix guru by any means and I want to upgrade these and enable GD etc, but I'm running 4 or more virtual servers by using the server tools and I don't want to break the builtin functionality of the server tools. Is apple going to upgrade this stuff on os x server?

Mac OS X Server ships with both Apache 1.3.33 and Apache 2.2 (in /opt/apache2).
You're more than welcome to disable Apache 1.3.x and use 2.2 if you prefer.
However, the Server Admin GUI will only currently work with Apache 1.3.x, so if you do you'll need to manage your configurations manually.

Mailman on Mac OS X Server 10.3.9 Problems

We have a few mailing lists on our old PowerMac G4/Dual 450 machine. We have Mac OS X Server 10.3.9 on there and we are using Mailman for list management.
Mailman is not sending anything through the lists. I repaired permissions via the Apple repair permissions function of Disk Utility and since there is a bug in that process in relation to Mailman I ran the check_perm -f command from Terminal to fix them to what Mailman wants. That usually fixes most of the problems with the Mailman system. Also restarted the qrunner and for a time that fixed it. But that isn't fixing it now.
I know the OS is old and we plan to replace it with a brand new X-Serve with Mac OS X Server 10.5.x. But for now the older server still needs to do its' job.
Any help would be greatly appreciated.
Thanks,
Ben

Yes and they show that the server received the message to the lists but I don't see anything being sent from the lists. I did a test message to one of our lists and got an error message back that said:
Your message
To: [email protected]
Subject: Helpdesk-users Reminder
Sent: Fri, 12 Sep 2008 10:48:37 -0500
did not reach the following recipient(s):
[email protected] on Wed, 17 Sep 2008 11:40:31 -0500
The e-mail system was unable to deliver the message, but did not
report a specific reason. Check the address and try again. If it still
fails, contact your system administrator.
< lists.sandburg.edu #4.0.0 X-Postfix; temporary failure. Command
output: couldn't connect to lmtpd: Connection refused_ 421 4.3.0
deliver: couldn't connect to lmtpd_ >
So how do I fix lmtpd?
Thanks,
Ben

Hosting a Domain Name on Mac OS X Server 10.1

Hello. I have a server running Mac OS X Server 10.1, and I
want to use it as a webserver. I already have a domain.
My questionis, how do i host the domain on the server?

The big difference between Mac OS X Server and client is that Server comes with a series of GUI tools for managing the server - configuring, stopping and starting the various server components including the web server, but also directory server, file servers and network services such as DNS, NAT, DHCP, etc.
There's no advantage to Mac OS X Server as far as PHP or MySQL is concerned - none of the GUI tools will drive those apps, so you'll need regular PHP and MySQL skills whichever way you go. If that's all you're using then Client should be sufficient.

Mac OS X Server - Web Hosting & Media Server

Hi All - Need advice. I have MacPro and have purchased MacPro Server.
Here is what I plan to do with MacPro Server:
1. Host couple of my personal websites, blogs etc.
2. Use it as a iTunes Media Server so that I can access my iTunes content through VPN / Internet remotely.
I want to use my MacPro largely for Web development work (basically as a DEV environment) whereas MacPro Server will be my Production environment. I have a couple of questions and will be grateful for your advice:
1. Is it a good practice to have iTunes Media Server on Mac OS X Server?
2. Presently, I have all my iTunes library stored on 2 x 2TB hard drives within MacPro. I would really like to move these hard drives to my MacPro Server and import the content to iTunes there. Can I do it? Will I lose the ratings and other details?
3. Will I be able to access iTunes on Mac OS X Server via Internet / VPN remotely?
Thanks in advance!!

By the way they are using Internet Explorer 7 when opening these documents.

Cannot open your default e-mail folders. You must connect to Microsoft Exchange with the current profile before you can synchronize your folders with your Outlook data file (.ost)

Fresh installation of Exchange Server 2013 on Windows Server 2012.
Our first test account cannot access their email via Outlook but can access fine through OWA. The following message appears - "Cannot open your default e-mail folders. You must connect to Microsoft Exchange with the current profile before you can synchronize
your folders with your Outlook data file (.ost)" is displayed.
If I turn off cached Exchange mode, setting the email account to not
cache does not resolve the issue and i get a new error message - "Cannot open your default e-mail folders. The file (path\profile name).ost is not an Outlook data file (.ost). Very odd since it creates its own .ost file when you run it for the first
time.
I cleared the appdata local Outlook folder and I tested on a new laptop that has never connected to Outlook, same error message on any system.
Microsoft Exchange RPC Client Access service is running.
No warning, error or critical messages in the eventlog, it's like the healthiest server alive.
Any help would be greatly appreciated. I haven't encountered this issue with previous versions of Exchange.

So it looks like a lot of people are having this issue and seeing how Exchange 2013 is still new (relatively to the world) there isn't much data around to answer this. I've spend ALOT of time trying to figure this out.
Here is the answer. :) - No I don't know all but I'm going to try to give you the most reasonable answer to this issue, in a most logical way.
First thing I did when I was troubleshooting this issue is that I ignored Martina Miskovic's suggestion for Step4 http://technet.microsoft.com/library/jj218640(EXCHG.150)because it didn't make sense to me because I was trying to connect
Outlook not outside the LAN but actually inside. However, Martina's suggestion does fix the issue if it's applied in the correct context.
This is where the plot thickens (it's stew). She failed to mention that things like SSL (which I configure practically useless - anyone who ever worked in a business environment where the owner pretty much trusts anyone in the company, otherwise they don't
work there - very good business practice in my eyes btw, can confirm that...) are some sort of fetish with Microsoft lately. Exchange 2013 was no exception.
In exchange 2003, exchange 2007 and exchange 2010 - you could install it and then go to outlook and set it up. And when outlook manual Microsoft Exchange profile would ask you for server name, you would give it and give the name of the person who you setting
up - as long as machine is on the domain, not much more is needed. IT JUST WORKS! :) What a concept, if the person already on premises of the business - GIVE HIM ACCESS. I guess that was too logical for Microsoft. Now if you're off premises you can use things
like OutlookAnywhere - which I might add had their place under that scenario.
In Exchange 2013, the world changed. Ofcourse Microsoft doesn't feel like telling it in a plain english to people - I'm sure there is an article somewhere but I didn't find it. Exchange 2013 does not support direct configuration of Outlook like all of it's
previous versions. Did you jaw drop? Mine did when I realized it. So now when you are asked for your server name in manual outlook set up and you give it Exchange2013.yourdomain.local - it says cannot connect to it. This happens because ALL - INTERNAL AND
EXTERNAL connection are now handled via OutlookAnywhere. You can't even disable that feature and have it function the reasonable way.
So now the question still remains - how do you configure outlook. Well under server properties there is this nice section called Outlook anywhere. You have a chance to configure it's External and Internal address. This is another thing that should be logical
but it didn't work that way for me. When I configured the external address different from the internal - it didn't work. So I strongly suggest you get it working with the same internal address first and then ponder how you want to make it work for the outside
users.
Now that you have this set up you have to go to virtual directories and configure the external and internal address there - this is actually what the Step 4 that Martina was refering to has you do.
Both external and internal address are now the same and you think you can configure your outlook manually - think again. One of the most lovely features of Outlook Anywhere, and the reason why I had never used it in the past is that it requires a TRUSTED
certificate.
See so it's not that exchange 2013 requires a trusted certificate - it's that exchange 2013 lacks the feature that was there since Windows 2000 and Exchange 5.5.
So it's time for you to install an Active Direction Certificate Authority. Refer to this wonderful article for exact steps - http://careexchange.in/how-to-install-certificate-authority-on-windows-server-2012/
Now even after you do that - it won't work because you have to add the base private key certificate, which you can download now from your internal certsrv site, to Default Domain Policy (AND yes some people claim NEVER mess with the Default Domain Policy,
always make an addition one... it's up to you - I don't see direct harm if you know what you want to accomplish) see this: http://technet.microsoft.com/en-us/library/cc738131%28v=ws.10%29.aspx if you want to know exact steps.
This is the moment of ZEN! :) Do you feel the excitement? After all it is your first time. Before we get too excited lets first request and then install the certificate to actual Exchange via the gui and assign it to all the services you can (IIS, SMTP and
there is a 3rd - I forgot, but you get the idea).
Now go to your client machine where you have the outlook open, browse to your exchange server via https://exchang2013/ in IE and if you don't get any certificate errors - it's good. If you do run on hte client and the server: gpupdate /force This will refresh
the policy. Don't try to manually install the certificate from Exchange's website on the client. If you wanna do something manually to it to the base certificate from the private key but if you added it to the domain policy you shouldn't have to do it.
Basically the idea is to make sure you have CA and that CA allows you to browse to exchange and you get no cert error and you can look at the cert and see that's from a domain CA.
NOW, you can configure your outlook. EASY grasshoppa - not the manual way. WHY? Cause the automatic way will now work. :) Let it discover that exachange and populate it all - and tell you I'm happy! :)
Open Outlook - BOOM! It works... Was it as good for you as it was for me?
You may ask, why can't I just configure it by manual - you CAN. It's just a nightmare. Go ahead and open the settings of the account that got auto configed... How do you like that server name? It should read something like [email protected]
and if you go to advanced and then connection tab - you'll see Outlook Anywhere is checked as well. Look at the settings - there is the name of the server, FQDN I might add. It's there in 2 places and one has that Mtdd-something:Exchange2013.yourdomain.local.
So what is that GUID in the server name and where does it come from. It's the identity of the user's mailbox so for every user that setting will be different but you can figure it out via the console on the Exchange server itself - if you wish.
Also a note, if your SSL certs have any trouble - it will just act like outlook can't connect to the exchange server even though it just declines the connection cause the cert/cert authority is not trusted.
So in short Outlook Anywhere is EVERYWHERE! And it has barely any gui or config and you just supposed to magically know that kind of generic error messages mean what... Server names are now GUIDs of the [email protected] - THAT MAKES PERFECT
SENSE MICROSOFT! ...and you have to manage certs... and the only place where you gonna find the name of the server is inside the d*** Outlook Anywhere settings in the config tab, un it's own config button - CAN WE PUT THE CONFIG ANY FURTHER!
Frustrating beyond reason - that should be Exchange's new slogan...
Hope this will help people in the future and won't get delete because it's bad PR for Microsoft.
PS
ALSO if you want to pick a fight with me about how SSL is more secure... I don't wanna hear it - go somewhere else...

Microsoft Exchange Server on Mac OS X Server

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