Kim Simmons (Customer) asked a question.
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When I have that error pop up, I find LEAP/Outlook are freaking out, because when they are trying to create the email, they doesn't know what to put into the subject line of the email. I bet when you close out of the error message, the draft email pops up, but there is nothing in the subject line. If you generate a letter for the same matter, it probably generates without the case name in the first Re line.
For me, this doesn't happen with every matter, but I have it happen frequently with estate administration cases. The solution I've found is opening the matter and clicking the spot that has the matter number and the staff assigned to the matter. It should open up the matter details box - click the Matter Title Tab - uncheck "Use Default" in the first re: line in Letters to Client and Letters to All Other Parties and type in what you want your usual subject like to be - I usually end up entering "Estate of Jane Doe" - this will be inserted in all correspondence, so make sure it's generic enough for all correspondence. Hit Okay. Now, if you try to generate an email from the matter it should generate a subject line in your email and open without the error message.