Emails Configured As HTML But Sent As Plain Text

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srmsrm

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
IMAP
I have Outlook 2016.

I generate all my emails in HTML. At times when I send my email it sends it as plain text (at least when I review the email in my Sent folder). I'm sending all my emails through my Gmail account.

I wish I could say when and why it happens, but I cannot. For example, I sent two separate emails this morning to the same person within a minute of each other. One went fine as HTML and the second went as plain text (they were very similar emails).

I cannot find any setting that indicates send only as plain text and the example I just noted above indicates it does work sending as HTML to the same person.

I do generate my emails using text from Quick Template (from MAPILab) and QuickText HotKeys (from Sperry). I have been using these programs for many years in Outlook 2010 without issue so I'm assuming these are not the issue.

At the top of the email, this is sample of what I see for an email send as HTML

MIME-Version: 1.0
Content-Type: multipart/alternative;
boundary="----=_NextPart_000_0054_01D32D4F.96CB5290"
X-Mailer: Microsoft Outlook 16.0
Thread-Index: AdMtcQJ4ehXblmXQQFKMXseQ+Ug9KQ==
Content-Language: en-us
This is a multipart message in MIME format.
------=_NextPart_000_0054_01D32D4F.96CB5290
Content-Type: text/plain;
charset="us-ascii"
Content-Transfer-Encoding: 7bit

Any ideas why this might happen?

Shawn
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
Are you using the same template each time?
At the top of the email, this is sample of what I see for an email send as HTML
you see this in the message body? if so, something is corrupting the message.

What antivirus/security software do you use? Does this only happen if you use the utilities to send mail or are "manually" created messages affected?
 

srmsrm

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
IMAP
Diane:

Avast anti virus. I do not have the Avast COM Add-In loaded.

Not sure what you mean by "Utilities". Assuming you mean the COM Add-Ins, I do not use any utility to send emails. I only use the COM Add-Ins for template text to populate the emails.

If I understand correctly, I manually send all my emails using what is provided in Outlook. I either reply to an email or select the email option for a contact and send the email.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
Not sure what you mean by "Utilities".
the quick template and hotkeys addins
I'm wondering if the template is set to plain text or if something in the process switches it top plain text. This is the most likely cause.

if you just hit reply to a message or use Ctrl+N to open a new message form and send it, does the format change?
 

srmsrm

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
IMAP
Diane:

Thank you.

When I press CTRL+N, it is set to HTML. I added some text with color, etc. and sent it to one of my other emails. It was sent as HTML.

The templates were created in Word (using the Quick Template Add-In) using color, font attributes, etc.

When I create a new email and use the template, I can see all OK before sending. The format is HTML. It is only after I send the email do I see the format change to plain text when I look at the email in the Sent box.

I did a test and created a new email and inserted text using one of my templates. I then saved it as a draft and all was OK. I closed Outlook, opened the draft again and still OK. I then sent the email. After I sent it and looked in my Sent box, it was plain text.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
look at the title bar when composing using the template - does it say HTML or Rich Text?
if rich text, it could be a setting in outlook that is converting RTF to plain text. This page shows where to check - Outlook is Sending Winmail.dat Attachments - you want it either on convert to html or leave it as RTF - but HTML is recommeneded as only other outlook users can see the formatting if you use RTF.
 

srmsrm

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
IMAP
Diane:

Thank you again for all your help.

The title bar does reflect HTML and in the ribbon HTML is highlighted as the format of the email. I am not sending any attachments and when the email is sent I do not see any attachments.

When I checked some contacts I am letting Outlook decide on the format of the email.

I don't know much about TNEF encoding, but maybe turn that off giving that a try? That was noted in the document you linked to concerning Winmail.dat Attachments but not sure if related or not.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
I don't know much about TNEF encoding, but maybe turn that off giving that a try? That was noted in the document you linked to concerning Winmail.dat Attachments but not sure if related or not.
It's worth a try - if it doesn't work, you can remove the key.
 

srmsrm

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
IMAP
Diane:

Gave it a try. No luck with disabling the TNEF encoding.

I have posted multiple questions due to issues I have encountered since upgrading to Outlook 2016. May I ask if you know of a link I can provide my comments to Microsoft? If yes, hopefully they may consider my feedback for future updates.
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
May I ask if you know of a link I can provide my comments to Microsoft?
suggestions go to outlook.uservoice.com - there don't have a good place for feedback/comments unless you use the insider build - then you'll have the option to report bugs/problems (file, support, contact support)
 

srmsrm

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
IMAP
Thank you. I went to the site and is it OK to enter what I think may be issues (maybe not suggestions)? For example, some of the items I noted was track changes in my draft (when Outlook doesn't have track changes), editing tasks in the Inbox, and imported ribbons being reset. These may be bugs or just suggested changes in functionality.
 

srmsrm

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
IMAP
Diane:

I think I figured out the issue thanks to your help.

One of the options in the QuickText HotKeys (from Sperry) Add-In is to add template text to the subject line of an email. I show these items as buttons in the ribbon and automatically text is added to the subject line once I click on the button. Example of buttons in the tool bar:

2.jpg


I walked through my normal process again of sending emails and noted as soon as added one of these subjects, the text "(HTML)" is removed from the email title bar. In the ribbon though, HTML is still highlighted. I sent a sample email and it was send as plain text.

I then reviewed all the template subjects and they all had extra lines in the default text. Once I removed all the extra lines, now the emails are being sent correctly. Now when I add in a template subject, the format "(HTML)" is not being removed from the title bar.

I manually tried to add extra lines in the email subject and I was unable to in the Outlook email.

I think for some reason the template subjects having extra lines was sending the email as plain text. No idea why. Now if this is a Sperry or Outlook issue, unknown. I will email Sperry and let them know what I encountered.

Thank you again for your help. Your guidance and suggestions allowed me to find the most likely fix for the issue I was encountering.
 
Last edited:

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
Subject lines don't properly support multiple lines...
 

srmsrm

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
IMAP
Diane, thank you. I'm guessing based on the Add-In adding a subject with multiple lines and Outlook not supporting is where the issue occurred. Thank you again for your guidance.
 
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