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Question

New Outlook / Smokeball Add-In pros and cons

  • August 21, 2026
  • 4 replies
  • 39 views

There are a couple of old threads about the “New Outlook” and Smokeball, but since they have old information and some refer to very specific issues, I decided to start a new one.  This is to help myself and perhaps others navigate the differences between Smokeball on the new outlook and the old one, given the fact that Microsoft now seems to be actively moving away from Classic Outlook such that it is now less functional than the new Outlook.

Here is my summary of the differences between the Smokeball experience on the two Outlooks.  Please correct me and update me:

  1. Linking multiple emails to a matter:  You can now do this on both old and new outlook.  New outlook provides suggested matters to link prior to your beginning a search, making the process faster in many instances.
  2. Linking matters in mobile Outlook app:  This was never supported when using the classic Outlook plug-in.  It was a promised feature for the New Outlook Smokeball add-in, but it appears to have been abandoned.
  3. Linking calendar appointments:  In classic outlook this can be done in the same manner as linking an email to a matter.  In new outlook this cannot be done.  The calendar appointment must be assigned to a Smokeball matter within Smokeball, not outlook.
  4. Adding attachments:  The “Attach Files” button in old outlook works quickly and reliably.  In the new Outlook, a separate window opens upon pressing the button and fails to completely load approximately 40% of the time.  Both the new and old outlook add-ins allow you to attach files upon initiating a new email from within Smokeball, and this process seems to work properly in both cases.
  5. Adding recipients:  The classic Outlook contains a “send to” button that allows you to add recipients from among the linked contacts within an associated matter at any time while composing an email.  This is not available in the new Outlook add-in.  Linked contacts from within a matter can be added as recipients only upon initiating a new email from within the Smokeball application.
  6. Forwarded emails and replies:  Due to the difference in adding recipients described in the previous paragraph, the new Outlook add-in provides no mechanism for adding Smokeball contacts to a forwarded or reply email.  Also, because of the difference in reliability of the attachment process (see paragraph 4), attaching documents to a forwarded or reply email is often problematic using the new Outlook add-in.
  7. pdf conversions:  The classic Outlook add-in allows a Word document to be attached to an email as a .pdf.  The new Outlook add-in does not provide for this.  The .pdf conversion must be done within Smokeball prior to attaching the document to an email.
  8. Archie email composition:  Both the new and old Outlook add-ins allow you to have Archie compose an email upon launching a new email from within Smokeball.  The new Outlook add-in also allows this after the email has been started in Outlook.  I have not used this function in either version, so perhaps there are other differences I cannot report on.

Please add your own observations or correct/update any of the above. 

I personally think that the Smokeball team needs to focus like a laser on getting the new Outlook add-in to function in a way that is as good or superior to the classic plug-in in every facet, since we are all going to be forced into the new Outlook soon.  Also, I suspect that ours is not the only firm that finds the Outlook integration to be the one feature of Smokeball that sets it apart from other potential solutions, and any backslide on this function causes us to question the rest of the relationship given the “beta testing” fit and finish to the whole package even many years into development...

4 replies

  • Contributor
  • August 21, 2026

Thank you for posting this!  The new outlook is giving me fits.   I hopw Smokeball is able to get the bugs works out soon!  


  • Contributor
  • August 21, 2026
  1. pdf conversions:  The classic Outlook add-in allows a Word document to be attached to an email as a .pdf.  The new Outlook add-in does not provide for this.  The .pdf conversion must be done within Smokeball prior to attaching the document to an email.

    This is a crucial feature that I believe Smokeball needs to focus on implementing into the new Outlook add-in. I can’t believe it’s not a feature yet. So many unnecessary saves and conversions now just to send an email of a draft document.

  • Contributor
  • August 21, 2026

The add-in is almost worthless for attaching draft documents from the matter to an email for client review. No attorney is sending a draft Word document to the client.


Michelle J
Smokeball Team
  • Smokeball Team
  • August 21, 2026

Hi all! I thought I'd add some extra information here for you.

I'm part of the product team here at Smokeball and want to assure you that the New Outlook add-in is a high priority for us at the moment. I'm actively working through building any missing functionality that is needed within it, and feedback like this is incredibly valuable in making sure we're aligned with users like yourselves on what matters most.

Some good news:

  1. The add-in is already available in the Outlook app on your phone. Here are the steps to get to it: Smokeball add-in on the Outlook Mobile App.
  2. We have also added some major improvements into the assigning flow, giving you the ability to rename your emails and attachments, choose their destination folders, or set a default folder so you don't have to change it every time: Save email and attachments modal

Looking ahead, we're currently working on the ability to convert your documents to PDF when attaching, along with improvements to that whole modal around search and sorting.

Surfacing matter contacts is close behind that as well as looking into supporting the addin across multiple mailboxes.

Keep your eye on the monthly product updates as we release new things, and please do keep the feedback coming. I'll keep an eye out here and can answer any questions that anyone may have 😊