Question Marks ? Appear in Sent Emails

Ernie:

Regarding sending attachments using Plain Text emails there's an issue with that as well. If you have text below the attachment (a signature for example) that text shows up as a separate attachment in Outlook with a "ATTxxxxxxx.txt" file name.

I have a pretty through analysis of these types of issues on the following thread. Feel free to read and chime in.

http://discussions.apple.com/thread.jspa?threadID=367990

My wife is experiencing this problem as well. I have read a few articles stating that this is due to sending mail in RTF and using double-spaces and having an MS Outlook client mis-read the extra space as a "?".

I can not confirm this statement because I sent myself some test emails using both plain text and RTF to my work email where I use Outlook XP on a Windows PC. I read and responded to both messages and neither showed a "?".

The messages I have viewed with this problem have double spaces. Example:

"end of sentence. Begin of new"
converts to
"end of sentence.? Begin of new"

I have also seen it in paragraph breaks. Example:

"End of paragraph"

"Start of new paragraph"

converts to

"End of paragraph"
?
"Start of new paragraph"

This is incredibly annoying and causing my wife fits. She uses her email for business and it's very unprofessional. I'm trying to make her comfortable using a Mac and this isn't helping.

Has Apple ever acknowledged this problem? I can't find any support docs covering it. Does anyone know the exact conditions on when this problem appears because I can not reliably reproduce it? Also, does anyone have a fix for this problem?

Thanks!

A client of mine also reported this problem with the ?-marks. It appears to be a recent phenomena. It's one that requires attention by Apple. It could render Mail useless in the PC dominated world.

iMac G3, G4, G5 Powerbook Mac OS X (10.4.4) iPods

Hello, and welcome to the Discussions.

Is you email account an IMAP or .mac, and is your Sent mailbox on the server? If so, then I believe the Mail Preferences/Viewing selection about displaying remote images might be in the mix. What is your selection for displaying remote images?

Ernie

The setting is to "Display remote messages in HTML." I think I will uncheck that setting.
Thanks for your help and response to my problem.

Peace,
Glen

iMac G3, G4, G5 Powerbook Mac OS X (10.4.5) iPods

Glen,

Not having it checked was one theory on why question marks were being seen in some Sent messages.

It could also have a bearing if messages received from some PC senders display the question marks.

I would appreciate more details on what your client's situation provides. I am not experiencing on any of my eight accounts, unless I uncheck that option.

More info, please, including whether accounts are POP, IMAP or .mac?

Ernie

ggarrett

I am using 10.4.5. However, this problem also existed in 10.4.4 as well.

I have narrowed it down that this problem occurs when Outlook reads the email in UTF-8 encoding. If there are double spaces between a sentence, it does it. If there is a space before a sentence, it does it. I have also noticed that it does it on symbols like the copyright symbol or fraction symbols.

If the Outlook read changes the text encoding to Western European (Windows), the question marks go away.

This is definitely an issue with Apple Mail and Outlook. I hve tested it using other mail clients (Windows & Mac) as well as online email clients (GMail, etc) and I do not get the question marks. I definitely welcome the opportunity to work with Apple to get this issue fixed.

Bronson,

Thanks your excellent analysis. My original reading of the first post of the Topic, was question marks appearing when checking one's own Sent message files -- a rereading may be that it is talking about replies to one's email sent to another?

Outlook is known to be a poor performer in dealing with Rich Text, when coupled with an Exchange server may send unreadable attachments on messages whether the recipient is using Macs or Windows, particularly if not also using mail clients that are of Microsoft origin.

MS, being a proponent of HTML, has poor support for Rich Text. If your wife would use only Plain Text and true attachments with messages to these Outlook users, I think there would be little problem. But, I would like to know any results of trying that. Like you, her, and many others, I would like to use Rich Text in a carefree manner, however.

So many of my friends love these mail enhancement hacks, but they make heavy use of HTML -- I wish they would not send that to me, even though I am always able to handle it in some manner or the other.

Keep providing us with your very useful comments, and conclusions.

Ernie

Bronson,

I have been writing about issues with text following attachments, even when only the Return key since 10.0, and even blank lines between multiple attachments -- it has been very well documented, by me and others.

Also, a message with Signature is not a Plain Text message if the Signature has content, itself, other than Plain Text. In Panther there was a separate preference for composing the Signature in Plain Text, I think, but in Mail 2.0, there is a convenient option in the pull-down under Format in the Menu Bar to "Make Plain Text" which has been provided for such situations, but perhaps more for sending to AOL, which cannot handle RTF very well, if at all.

What is interesting to me, is that I used have an old PC running Windows '95 set, using a Netscape mail client, and it always handled anything OSX and Mail could throw at it, even when only 10.0, and before Windows Friendly, and other options we have discussed were available.

All the best,

Ernie

Glen,

To be sure, I am very interesting in your problem, and I for one, have been very strident to Apple about needed changes, and have some very good avenues of feedback. However, I can do very little more without actual examples of messages exhibiting this problem. If you, rather than a client has this problem, then please conduct some tests with me, so that I can contribute to the resolution. I myself receive very few messages than I cannot resolve handling for.

Ernie

Ernie:

Regarding text after an attachment, in the tests I have done, the text after the attachment was plain text. I made sure that I was sending a pure text email with an attachment. I would type text above the attachment, include the attachment, then add text below. Each time, the text below came through as a separate attachment.

Interestingly, the workaround is to send a true RTF email with formatted text (like a formatted signature). In that scenario, the email came through as expected. Now, I was only testing image files. I don't know if it's different using DOC or PDF files.

If you would like to setup an offline dialog to continue testing please let me know.

I have come across another intersting problem you may be able to help with. My wife is sending her sister some pictures. The pictures are not getting to her sister. As a test, she sent the pictures to both her sister and me (at work with Outlook behind and Exchange server) and I receive them just fine. So, the emails are obviously leaving the computer with the attachments.

Here's the weird part. I can reply to the email I received with the attachment and include her sister on the reply, she then receives the images. WEIRD!!

Now, I am convienced that this is not a Mac or Apple Mail problem. It must be something with her sister's ISP stripping the attachment before she receives it. The problem is that it started at the same time we got the Mac. Coincidence???

Have you heard of anything like this?

Bronson,

I have been out all evening, and only just returned. I will get back to you on your offer to test, which is very much appreciated.

Look at the Long Headers of a message from her sister, to check for any header relating to virus scanning. Is there any chance the message size would be enough for the photo attachments, but they are not being seen?

Later,

Ernie

I'm seeing the same issue, but not with question marks: I get an upper case B, but sometimes that Scandinavian A with a circle on top. It seems to happen when someone running Outlook replies to one of my emails. Here's an example of an email which I sent to a friend; she replied, and quoted my original text, as such:

Blah blah blah sentence 1.Â

Sentence 2. Sentence 3. Sentence 4.Â

Yours, etc...

These characters may appear at the end of sentences, or at the end of paragraphs. This happens routinely when someone using MS Outlook replies to my emails.

Luke,

Thanks for this description. Until I received an email from Glen, I had thought the question marks were those used as placeholders for embedded images, but in that email I found what you report, except for the actual character, but have not found the actual cause.

In light of this information, I am suspicious of the way quoted text and level of quoted text is handled. In Mail Preferences/Composing, what are your selections in the section for Responding?

Ernie