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AutoDiscover Configuration For Exchange 2010

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Home / AutoDiscover Conguration for Exchange 2007 and 2010

AutoDiscover Conguration for Exchange 2007 and 2010

Posted on March 5, 2012 by Tom Finnis in Exchange Server with 0 Comments

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Overview
The AutoDiscover feature in Exchange 2007/2010 is often overlooked during setup but is an important factor in ensuring
smooth day to day running of your Exchange environment. Its main function is to provide the mail client with all the
conguration options it needs, from only the users email address and password. This is particularly useful for remote users

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and smartphone users, who no longer have to enter advanced settings like server names and domains. It is also vital for the
correct functioning of features such as Out Of Oce and the Oine Address Book in Outlook.
AutoDiscover simplies email client conguration for remote and mobile users; you may not have noticed it but most email
clients nowadays will simply ask for your email address and password rst, e.g. the Android email setup screen:

Email Address

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What actually happens after you have entered your details is that the client looks for autodiscover.yourdomain.com and
attempts to retrieve the rest of the server conguration details from there. If youve set that up properly then no more
information is required, making the setup process very simple for non IT-literate users and saving you from having to deal
with support calls.
The second main function of AutoDiscover in Exchange is linked to the Oine Address Book and Out of Oce settings,
as Outlook uses part of Outlook Web Access for them, rather than the MAPI based connections used for mailbox access. The
Outlook client actually uses the AutoDiscover address to retrieve the Exchange Server details for these, so if it is incorrectly
congured you may nd these features dont work, even though everything else does.

Why is AutoDiscover Important?

The Exchange setup process doesnt mention AutoDiscover, and the ocial Microsoft documentation doesnt really stress the
importance of it either, so it can easily pass you by. As part of the general OWA setup the Exchange installer creates an
AutoDiscover folder and adds the internal URL to the Exchange conguration, so if your network consists of a single site with
local desktops then it should work ne for you.
However, if you want easy email setup for mobile and remote users, or if your users are unable to set Out of Oce via
Outlook but it works in OWA, then you may well need to check your AutoDiscover conguration.

How to Check Your AutoDiscover Conguration

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AutoDiscover Configuration For Exchange 2010

How to Check Your AutoDiscover Conguration

There are two tests you need to run to check that you have your AutoDiscover conguration correct, one from outside your
network and one from inside. The outside test is probably the easiest so lets do that rst. Open
www.testexchangeconnectivity.com in your browser. By the way, if you havent encountered this website before then add it to
your Bookmarks; its an exceptionally useful tool for various Exchange diagnostics. Its provided by Microsoft so it should be
safe to trust with condential information, but make sure you check the sites SSL certicate rst to make sure you are at the
correct one!

You will notice that there are two AutoDiscover tests listed, one for ActiveSync and one for Outlook, but in fact for this test we
are only really interested in the AutoDiscover part which is the same for both. All the same, you may as well select the one
which is more relevant for you now and click Next, then on the next page ll out the information requested. You dont have to
enter a valid user account and credentials but if you do then it can test the process all the way through, so I would
recommend it. You will also see there is a check box for Ignore Trust for SSL; for the moment its easiest to tick this, well
cover certicates later. Once you have done that and worked out the validation code you can clickPerform Testand wait for
the results page.

Chances are you will see a results page like the one above, which doesnt tell you much, so click on Expand All for more
details. You will see that it has run a whole bunch of DNS lookups and tests, no doubt most of them have failed but dont
worry about it too much for now as we will go through how to congure it shortly.
To test your AutoDiscover from inside your network the easiest way is to use a copy of Outlook 2007 or 2010 that is already
setup and connected to your Exchange Server. Look down in the SysTray by the clock and locate the Outlook icon there, then
hold down the Ctrl key and right-click it for the extended menu you will see that Test Outlook AutoConguration is an
option so click that.

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AutoDiscover Configuration For Exchange 2010

In the window that opens, your email address should already be entered so just add your password and make sure that only
the Use AutoDiscover box is ticked, then click Test. The Results box should ll up with a bunch of text, look closer and you
will see that it is split into two sections: Exchange RPC and Exchange HTTP, each with URLs for things like OOF (Out Of Oce)
and OAB (Oine Address Book). It should go without saying that these URLs should be resolvable from your internal network
clients, or else you will have a problem!

Dealing with Common AutoDiscover Problems

There are usually just two common causes for AutoDiscover to not work, and the tests above will show clearly if you are
suering from one of them. The rst problem is DNS resolution; either you do not have a DNS A record setup for
autodiscover.yourdomain.com or it is resolving to the wrong address. Note that there are two dierent DNS resolutions
involved here: the public DNS for external clients and the internal DNS for your network clients. If the Microsoft Remote
Connectivity Analyzer website is showing a DNS resolution failure then it is referring to your public domain DNS record, which
you probably have hosted at the same provider as you purchased your domain from, or another third party DNS service. The
easiest way to check the public DNS record is using a website such as www.kloth.net/services/nslookup.php here I am
checking for the Petri.co.il A record:

If you have completely forgotten where your domain DNS is hosted then you can also use this site to nd out just put in
your domain name by itself and select NS (Nameservers) as your query:

The nameserver query will tell you the domain name of the DNS hosting service, and from that you should be able to get
access to your DNS management with a little eort. Dierent DNS services have variations in their management interfaces
but the basic principles are the same; you will need to create or edit the A record for autodiscover.yourdomain.com so that
it points to the public IP address of your Exchange Server. You may need to wait a few hours for the change to propagate but
then when you run the MS Connectivity test again it should report a successful resolution of the AutoDiscover address.
For your internal network clients xing the DNS resolution should be even easier, as you will have your own internal DNS
server, so you just need to open up the management console for that and add in the appropriate A record to resolve to the
internal address of your Exchange Server. Once you have changed it you can try the Outlook Email AutoConguration test
again, however make sure the DNS cache on your local machine is updated rst, either by simply rebooting it or running
ipcong /ushdns from a command prompt.
The remaining two problems you may encounter will only aect external clients, but usually those are the ones you want to
make things easiest for, as you wont be there to assist them most of the time. You need to make sure that your Exchange
Server is accessible for https on port 443 by conguring your rewall appropriately, although if you already have Outlook
Web Access working for external users then you will have done this step already.
The next error you may encounter from the MS RCA website is common enough that it deserves its own section.

Solving Problems with Your SSL Certicate

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Often the main problem with your SSL certicate isthat the name does not match. This usually occurs if you are using a selfgenerated certicate, or have purchased a basic single name certicate for OWA access, which might have a name like
webmail.yourdomain.com. Now you can decide to just ignore this, if you only have a few users to worry about then you may
well feel that the additional expense of a new certicate is not worth it. However an increasing number of mobile devices and
mail clients will refuse to accept an unveried certicate nowadays, which is a sensible security measure, however it means
you have to install your CA (Certication Authority) server certicate manually which can be a pain and defeats the purpose of
AutoDiscover in the rst place. The solution Microsoft recommends is to purchase a SAN (Subject Alternative Name)
certicate, which allows you to register several DNS names on one certicate. Nowadays there are some certicate vendors
who oer very cheap or even free certicates, but personally I prefer to stick with the well known trusted CAs like Digicert,
who also have useful installation guides and utilities on their website.
For internal network clients, provided they are domain members, the SSL certicate should not be an issue as they will
automatically trust your internal CA if you have self-signed. The only occasion it may be an issue is if you have installed a
certicate for your public domain name (e.g. yourdomain.com) but you have a dierent internal domain name (e.g.
yourdomain.local). In this situation the easiest solution is to change the internal AutoDiscover URLs to match your public
domain name, and ensure you have the correct A records in your internal DNS resolving to the internal IP of your Exchange
Server. In Exchange 2007 this requires a few PowerShell commands, rather than repeat them all here, the process has been
well described in this MSExchange.org article. In Exchange 2010 the process is a little dierent but again has been covered in
another MSExchange.org article.

Completing Your AutoDiscover Conguration

Once you have worked your way through the above steps you should be able to successfully test your AutoDiscover
conguration both externally and internally. If you had experienced problems with your Oine Address Book in Outlook
before, or users could only set their Out of Oce by using OWA then you should nd that these problems have been solved
as well. The best part though is how easy it becomes to set up new mail clients and smartphones, in fact most users should be
able to do it themselves now without having to seek your assistance!

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