Why is Mail attaching replies as .html or .txt documents? (Exchange 2013 EWS)

Late 2014 Retina MacBook Pro (2.5 GHz i7, 16 GB RAM, Nvidia GeForce GT 750M 2 GB)
Mac OS X 10.10.4 Yosemite
Mail.app 8.2 (2102)
Exchange Server 15.0.516.032 (2013)

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I'm a law student at a university that uses Google Apps, I work for an organization that uses Exchange, and I use Gmail and iCloud for my personal email. As such, Mail.app is a huge part of my workflow. Because of this, using a separate application (e.g., Outlook 2016) just for my work email or migrating all of my accounts to Outlook 2016 doesn't really make sense.


At work, we have a mixed Windows 7/Mac OS X environment, with most users toting work iPhones.


Recently, I've been made aware that when I reply to or forward work email, Mail.app is removing the previous replies from the body of the message and attaching them as either an .html or .txt file instead of appending them to the body of the message. On my MacBook and iPhone (running iOS 8.4), the previous replies are still visible in the body of the message. Since my PC-using colleagues are not used to opening attachments to see previous replies, this leads to a flurry of messages (e.g., "Wait, what was this about?", "Could you please reply to the thread?", etc.) back to me.


If I reply using Outlook 2016 on my MacBook (main work computer), Mail on my iPhone, or the ancient PC at my desk, the replies are appended in the body of the message, as is expected behavior.


What I've Tried:

  • Sending messages from Mail.app as plain text. (previous replies were attached as a .txt document instead of .html).
  • Copying and pasting previous replies into new messages (with the same subject, so as to preserve threading) (previous replies attached as before, not appended in the message body)
  • Updating my settings in OWA to plain text. (no real change, since this would likely only affect messages sent directly through OWA).

Thoughts? I've reached out to our guys here for help, too.

MacBook Pro with Retina display, OS X Yosemite (10.10.4)

Posted on Jul 31, 2015 10:55 AM

Reply
2 replies

Aug 1, 2015 2:25 PM in response to Eric Root

Hi Eric, and thank you for your reply.


I thought I had marked this as resolved; my apologies.


The root of this issue a continued inability on the part of Outlook/Exchange to follow industry standards. Outlook/Exchange is unable to parse messages that include in-line attachments. By setting Edit > Attachments > √ Always Send Windows-Friendly Attachments; √ Always Insert Attachments at the End of Message, the problem seems to mostly resolve itself. Previously, I had Windows-Friendly turned on, but my attachments were being inserted below my signature line (and above previously quoted text).


Others have suggested changing the default message format to "Plain Text," but I haven't noticed an improvement.


Another alternative is to include links to attachments (Mail Drop or Dropbox) as opposed to actually attaching files.


Replies are threaded/appended correctly if no in-line attachments are included or if attachments are inserted at the end of the message.

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Why is Mail attaching replies as .html or .txt documents? (Exchange 2013 EWS)

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