Outlook Connectivity Guided Walkthrough (Exchange On-Premises)

Outlook prompting users for credentials? Outlook users disconnected from their mailboxes? These are a couple of common issues and they can be frustrating to the user. Enter the Outlook Connectivity Guided Walkthrough (GWT).

Outlook connectivity issues with Exchange server can be a very frustrating for both the user and the administrator. Unfortunately, connectivity issues aren’t uncommon and will likely occur at some point in time whether your mailboxes are hosted on-premises, in Office 365, or a combination of both, i.e. Hybrid setup. Earlier this year we released a guided walkthrough for Outlook connectivity issues in Office 365.

To assist you in troubleshooting Outlook connectivity issues in an Exchange on-premises environment, we’ve now released the Outlook Connectivity Guided Walkthrough (GWT). You can use this walkthrough for troubleshooting some common issues which include:

  • Prompts for credentials
  • Certificate errors
  • Client disconnects
  • Offline Address Book download issues
  • Autodiscover issues


The goal for this guided walkthrough is to help you resolve Outlook Connectivity issues with Exchange in a timely manner by providing troubleshooting steps in a logical manner depending on the symptoms of the issue being experienced.

I’d like to thank everyone who contributed to the development of this troubleshooter with special recognition going to the following folks: Victor Zhang, Sainath Vijayaraghavan, Melissa Grewing, Shaun Gimberline and Amir Haque.

Jim Martin

Comments (12)
  1. Anonymous says:

    I am so glad to hear I’m not the only one battling my ass of with this damn thing. Why? Why does MS take something that works well and in the name of simplifying things they go and complicate the hell out of everything and in the process make it almost

  2. drb19791 says:

    Nice, but most of your on premise customers would prefer resources dedicated to fixing the core issues with Exchange 2013. Its apparent from recent posts on this blog that the Exchange team still do not appreciate the frustration and concern that its customers have.

  3. ABCFED says:

    The tool is nice, yes, but since Exchange 2013 can't handle message formatting correctly, still has certificate issues, half the GUI features of Exchange 2010 are missing, and more (just read the last post comments)…it's kind of silly.

    I would also prefer if the Exchange team would stop wasting their time on these tools and perhaps…maybe…fix the base product…so…you know…it actually works right?

    Not that there is anything wrong with this tool. It's neat, but…damn the tool. I want Exchange to work right first.

  4. Durval Ramos says:

    I share the idea of ​​both

  5. Rhys says:

    Spent a few hours trying to fix a new Exchange 2013 CU2 using that. It confirmed somethings wrong, but it doesn't link to any helpful information or a way to fix it. Searching technet for the results just leads to other people asking the same question for the same fault. This tool can't fix a faulty product.

  6. Upset Customer says:

    I have to agree with ABCDEF, it would be nice to see some effort going into fixing Exchange 2013 – many customers like myself are suffering daily from issues in it that we have been told will not be fixed until CU3 and no HF would be released….

  7. Just added my comments to Perry's previous blog.

    I thought I had mastery of these issues in Exchange 5, 5.5, 2000, 2003, 2007 and 2010.

    All of a sudden I need a walkthrough. Look at Perry's blog and the questions. We are experienced Exchange admins. We are (were?) your fans.

    Somehow you have got into a situation now need to explain to us how to do all the things we already thought we knew about!

    I am aware that we are not getting any younger, but why do we have to start again with Exchange 2013 and Office 365?

  8. Waspy says:

    The most annoying thing (in our company) are the cached credentials in the password vault.

    And sometimes we have hardware developers, who entered their own proxy into the IE….

    But thats another topic :-)

  9. ktookes75 says:

    Excellent troubleshooting tool! Thanks for sharing.

  10. Thanks, but what gives? says:

    Nice post but why not one reply to the previous post of "The Road Ahead"?  You have a bunch of Exchange Admins asking legitimate questions and they are simply being ignored.  Loved Exchange 2007 and 2010 but still don't see a reason to move to 2013 with all that I've been hearing.  I know you guys are working hard but I think it's in the wrong direction.  Just my two cents.

  11. 13 outlook says:

    don't waste your money – maybe it was made in china; the support team really – translation your on your own. no support here. refund time!!!

  12. What does it matter says:

    Yup what does it matter that Exchange 2013 doesn’t work straight out of the box. Microsoft wants everyone to go to the Cloud that this poor rendition of Exchange (2013) is effectively trying to stealthily force migration so Microsoft can then parse emails
    in the cloud and sell more advertising. If you make it impossible to configure you’ll lose your audience. Factually I am going to write to Bill Gates and ask him to himself sit down and do an install of Exchange 2013. It is only then that the pressure will
    come for you guys to learn to make a product that is usable! This is a bad joke of a product (Exchange 2013) and my migration path has been nothing but hell.

Comments are closed.