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Gotchas with Server-Side Sync and the New Outlook App

I am trying to deploy the new server-side sync Outlook app to my organization. Running into some "gotchas" I haven't seen documented elsewhere...all of which make the SSS app seem unready for enterprise deployment. Security issues, UI issues, reporting issues. Maybe y'all can help?

Gotcha #1 (App) – Disappearing “Tracked” Status

We configured the app as described in the Deployment Guide ( Manual tracking for incoming messages works okay...most of the time. However, it is common for the tracking status to appear to revert itself within the app. It goes like this:

  1. I go through all the steps to track the message
  2. The bar in the app says "Tracked RE: XYZ Opportunity"
  3. I navigate away from the message
  4. I come back to the message and reopen the app
  5. The bar in the app just shows the "Track" button as though I had never tracked the message in the first place
  6. I become irritable

This occurs even when I can see in CRM that the message has been promoted. So the tracking is working, I think, but the UI in the app doesn't show the accurate tracking status. This has happened in reverse, too – sometimes the app insists that a message is tracked, but the message is not in CRM.

This is especially annoying when paired with Gotcha #2…

Gotcha #2 (App) – No Quick View for Tracked Messages

The old Outlook plugin used to show a handy icon in the Outlook inbox/outbox/folders to indicate which messages have been tracked to CRM. With the new app there is no icon. Nor any other way of easily viewing which items have been tracked, as far as I can tell. It seems like they want you to navigate to a given Outlook item, open the app, and look at the tracking status…and hope that Gotcha #1 hasn’t gotten you this time.

Anyone have a workaround so that your staff can more easily review their tracked messages?

Gotcha #3 (SSS) – Can’t Tell Who Tracked a Message

With the old Outlook plugin, messages tracked to CRM appeared as “Created By” the user who tracked them. This was helpful in troubleshooting, and in understanding user adoption.

However, incoming messages tracked with the new app via server-side sync appear in CRM as “Created By” SYSTEM. Per the Premier tech with whom I have been working, the “Owner” for SSS tracked messages is assigned by running through the “To” list to see if any of the recipients were owners of messages earlier in the chain. It assigns to the first match it finds based on whatever order the recipients happened to load into the database array – or to the last item in the array if the algorithm didn’t find a match.

The “Owner” on SSS tracked messages therefore doesn’t have anything to do with the mailbox from which the message was tracked. The Premier tech said there is no way to see who tracked a message when using SSS.

How do you manage activity user adoption and reporting when using SSS?

Gotcha #4 (SSS) – Settings to Check Before You Deploy SSS

So the app was working in our QA environment, aside from the items listed above. When we tried to launch the app to another small group of users in Production, though, things started going wrong. Like "thousands of messages got promoted to CRM that never should have been there" wrong.

Below are some details you should be aware of that are not in Microsoft’s app deployment guide. As far as I can tell, these apply to server-side sync -- whether you are using SSS with the new Outlook app or the old COM Add-In.

NOTE: The information below is from my Premier tech, and corroborated in many places online. Following these guidelines has not fixed my problem, though. Take the info below with a grain of salt, test in your sandbox before deploying to production, etc. It’s currently unclear whether the info itself is wrong, or whether I am in a break-fix scenario that we have not yet diagnosed.

When you enable a CRM mailbox for SSS, messages will get probably promoted into CRM that your staff did not specifically track. What messages get promoted depends on the following configurations date and subject/recipient correlation matching. This encompasses both system settings and user settings, so you need excellent user compliance to avoid an undesirable outcome.

System Settings – “Process Email From” Date

In System Settings > Email Configuration > Email Server Profiles > [your default server profile] > Advanced > “Process Email From” Date

This “Process Email From” date looks at all messages in your users’ Outlook that were modified on or after the date. Modified, in this case, could be something like moving the message from one folder to another in Outlook, adding a category tag, or flagging/unflagging a message.
If the recently modified messages also meet the criteria in the correlation and user settings, they will get promoted into CRM.

System Settings – Correlation and Smart Matching

Folder level tracking and tracking tokens are not a good match for my organization, so we have had Smart Match correlation turned on. This wasn’t doing anything when we had the old Dynamics 365 for Outlook plugin; replies in a tracked thread were not getting promoted to CRM. With SSS, though, this setting combined with the “Process Email From” date and the “Select Messages to Track in Microsoft Dynamics 365” settings to promote even more unintended messages into CRM.

User Settings – “Select Messages to Track in Microsoft Dynamics 365” and “Automatically Create Records in Microsoft Dynamics 365”

In user settings Gear Icon > Options > Email tab > “Select the messages to track in Microsoft Dynamics 365” ( describes how these options operate with the old Dynamics 365 for Outlook plugin, but things get more complicated when you add SSS)

The default option is “Email messages in response to Dynamics 365 email”. Any message that meets the date requirement in the system setting above and that CRM thinks is part of a previously tracked conversation will get promoted into CRM when you test&enable the mailbox for SSS. “Part of a previously tracked conversation” depends the correlation/smart matching/tracking token criteria. This is the most restrictive option – there is apparently no option for “oh hell no please do not promote anything into CRM that I have not specifically tracked”.

All email” is a bad idea. Don’t do it.

Email messages from Dynamics 365 Leads, Contacts, and Accounts” could theoretically be a good idea if you never discuss anything confidential or personal with your customers. However it’s a recipe for disaster when paired with the other item on the personal email settings page: to automatically create Contacts, Leads, or Accounts from incoming email. If your colleague has the latter setting turned on, and they receive an email from you, then you get created as a Contact in CRM. And then all your emails could get automatically promoted into Dynamics when SSS gets enabled for your mailbox. Customer email, personal email, confidential correspondence, all of it.
“Email messages from Dynamics 365 records that are email enabled” is like the Contacts/Leads/Accounts option above. But it also extends to any other OOB or custom entities that contain an email-type field.

Administrators have limited control over user settings. The “User Settings Utility” in XRMToolbox allows you change the personal email settings for your users. The “User Settings Utility” does not let you inspect your users’ current settings, though, so for troubleshooting you can never be 100% sure what a user’s setting was at the time of an error. And there is no way to prevent a user from changing their personal email settings again once you have set the desired default.

This seems like a security gap. In theory, there must be a magic combination of these things that prevents CRM from promoting personal emails without consent. I haven’t found it yet. But there are other folks who have been using SSS and the Outlook app, and are happy with it – so I hold out hope that there is a solution.

How do you prevent sensitive messages from unintentionally being tracked to CRM? Is it possible to turn off the portions of the synchronization completely, and still have the app work for people to manually promote their messages to CRM?

Background Information

Details for anyone who wants to help troubleshoot: We are on the most recent version of CRM Online, Windows 10, and Office 2016.

We used the old Microsoft Dynamics for Outlook COM Add-In with its built-in email sync tool for a few months, but my IT dept has stopped supporting it because it was crashing so many computers, and MSFT was no help in resolving the issue. Folder level tracking is not a good fit for my org.

That’s the reason we are trying to move to the new Outlook app with SSS. I am solution agnostic, though. Open to any creative ideas that allow my staff to track their emails and appointments to CRM without needing to leave their email program.


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Tags Server-Side Sync and the New Outlook App