AutoDiscover Configuration for Exchange 2010

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    AutoDiscover Con㜀guration for Exchange 2007 and 2010Posted on March 5, 2012 by Tom Finnis in Exchange Server with 0 Comments

    S h a r e          T w e e t        P i n i t          R e d d i t        S h a r e          S h a r e        

    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

    con㜀guration options it needs, from only the user’s email address and password. This is particularly useful for remote users

    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 O ce and the O㔀ine Address Book in Outlook.

    AutoDiscover simpli㜀es email client con㜀guration 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 㜀rst, e.g. the Android email setup screen:

    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 con㜀guration details from there. If you’ve 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 O㔀ine Address Book and “Out of O ce” settings,

    as Outlook uses part of Outlook Web Access for them, rather than the MAPI based connections used for mailbox access. TheOutlook client actually uses the AutoDiscover address to retrieve the Exchange Server details for these, so if it is incorrectly

    con㜀gured you may 㜀nd these features don’t work, even though everything else does.

    Why is AutoDiscover Important?

    The Exchange setup process doesn’t mention AutoDiscover, and the o cial Microsoft documentation doesn’t 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 con㜀guration, so if your network consists of a single site with

    local desktops then it should work 㜀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 O ce via

    Outlook but it works in OWA, then you may well need to check your AutoDiscover con㜀guration.

     

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    How to Check Your AutoDiscover Con㜀guration

    There are two tests you need to run to check that you have your AutoDiscover con㜀guration correct, one from outside your

    network and one from inside. The outside test is probably the easiest so let’s do that 㜀rst. Open

    www.testexchangeconnectivity.com in your browser. By the way, if you haven’t encountered this website before then add it to

    your Bookmarks; it’s an exceptionally useful tool for various Exchange diagnostics. It’s provided by Microsoft so it should be

    safe to trust with con㜀dential information, but make sure you check the site’s SSL certi㜀cate 㜀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 㜀ll out the information requested. You don’t 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 it’s easiest to tick this, we’ll

    cover certi㜀cates later. Once you have done that and worked out the validation code you can click Perform Test and wait for

    the results page.

    Chances are you will see a results page like the one above, which doesn’t 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 don’t

    worry about it too much for now as we will go through how to con㜀gure 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 AutoCon㜀guration is an

    option so click that.

    http://www.testexchangeconnectivity.com/

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    In the window that opens, your email address should already be entered so just add your password and make sure that onlythe Use AutoDiscover box is ticked, then click Test. The Results box should 㜀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 O ce)

    and OAB (O㔀ine 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

    su爀ering from one of them. The 㜀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 di爀erent 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 㜀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 e爀ort. Di爀erent 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 㜀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 AutoCon㜀guration testagain, however make sure the DNS cache on your local machine is updated 㜀rst, either by simply rebooting it or running

    ipcon㜀g /㐀ushdns from a command prompt.

    The remaining two problems you may encounter will only a爀ect external clients, but usually those are the ones you want to

    make things easiest for, as you won’t 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 con㜀guring your 㜀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 Certi㜀cate

    http://www.kloth.net/services/nslookup.php

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    Often the main problem with your SSL certi㜀cate is that the name does not match. This usually occurs if you are using a self-

    generated certi㜀cate, or have purchased a basic single name certi㜀cate 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 certi㜀cate is not worth it. However an increasing number of mobile devices and

    mail clients will refuse to accept an unveri㜀ed certi㜀cate nowadays, which is a sensible security measure, however it means

    you have to install your CA (Certi㜀cation Authority) server certi㜀cate manually which can be a pain and defeats the purpose of 

    AutoDiscover in the 㜀rst place. The solution Microsoft recommends is to purchase a SAN (Subject Alternative Name)

    certi㜀cate, which allows you to register several DNS names on one certi㜀cate. Nowadays there are some certi㜀cate vendors

    who o爀er very cheap or even free certi㜀cates, 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 certi㜀cate 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

    certi㜀cate for your public domain name (e.g.  yourdomain.com) but you have a di爀erent 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 di爀erent but again has been covered in

    another MSExchange.org article.

    Completing Your AutoDiscover Con㜀guration

    Once you have worked your way through the above steps you should be able to successfully test your AutoDiscovercon㜀guration both externally and internally. If you had experienced problems with your O㔀ine Address Book in Outlook

    before, or users could only set their Out of O ce by using OWA then you should 㜀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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