Leopard Mail’s drag-n-drop double act (with MailTags)
Like many people (but apparently not all), when I drag an item from the Finder to Mail.app’s Dock icon, it launches two messages, the first without the attachment, the second one with it.
Obviously, this is annoying and I have always regarded it as just that. However, today, a poster on the Apple Discussion Forums 
points out an even more annoying aspect of this new “feature” in Leopard Mail:
If I drag a file from Finder to Mail icon in Dock, Mail opens and creates two windows. I write my message in the window in front.
Then I get interrupted, and when I come back I need to write another message to a different recipient before I complete the first message. I use the second window for this message (convenient as it is already there…) I place a different file in this message and send it. My first message window then disappears!
Fine, I think – I´ll write it again. Only, it turns out that the recipient of my SECOND message received the FIRST message, including attachment and everything written in the body area (not in subject area). I work with clients for whom discretion is important – this is risky as sensitive information can end up in the wrong places!!!
Hmmmm… Maybe it is a good idea to use the Attachment button in the Toolbar until this one gets fixed.
UPDATE: Johann suggests in the comments that this is a MailTags problem. Testing — the kind of testing that one should do before pushing out a blog post — clearly demonstrates that it is (for me anyway), based on a statistical sample of one. But Scott knows about it, which means that will probably be fixed even before this update is posted!
UPDATED UPDATE: The controversy continues. The original poster and many others claim that they get this behaviour without MailTags installed. Follow it blow by blow in the Apple Discussions.
UP-TO-DATEST UPDATE: Glenn posts in the comments that this is a bug in Leopard Mail and quotes Apple’s response to his submission of a bug report:
This is a follow up to Bug ID# 5630858. After further investigation it has been determined that this is a known issue, which is currently being investigated by engineering. This issue has been filed in our bug database under the original Bug ID# 5243377.
Similar Posts:
- Emailing a file with Quicksilver
- Email a file directly from Finder
- Leopard Mail.app and plugins: Trial and error
- Photo Cluster: free stationary for Leopard Mail
- 111 extra HTML stationery templates for Leopard Mail
Tags: Apple Mail, attachments, bugs, leopard mail, mail.app
December 5th, 2007 at 11:50 pm
This is a MailTags issue. I posted about it on the indev.ca forums, and Scott Morrison replied that he’s already aware of it:
http://indev.ca/forum/viewtopic.php?t=1097
December 6th, 2007 at 12:07 am
Thanks. You’re quite right. I should have thought to check that.
December 6th, 2007 at 12:13 am
Is there any hope that Apple will sooner or later provide a clean and officially supported add-on framework for Mail? :roll:
December 6th, 2007 at 12:22 am
Nope ;-)
December 6th, 2007 at 3:14 am
I’m having this problem too. I don’t have MailTags installed. But, I did under Tiger, and I used the migration assistant to move my data.
December 6th, 2007 at 4:44 am
I have never had MailTags installed – and I have this same issue.
December 6th, 2007 at 5:21 am
I don’t have Mail Tags installed either, and I encounter the same problem, including the switched mail phenomenon described above. (German localization, btw.)
I’ve sent massive feedback to Apple, including samples of my mails for downloading, which I include here. (If the blog admin thinks this to be unnecessary, please feel free to edit my comment accordingly.)
Hello,
recently, I sent feedback about how Mail (the app) creates two mails (“mail A” and “mail B”) instead of just one when a file (“file A”) is dragged onto the Mail Icon in the Dock. Mail B is created first, Mail A above it, Mail A then contains the file “A”, (hence I chose to name this one “A”.)
Now, I’ve got additional feedback on that subject: The second mail form (“B”, the one created first) is unusable. In my case I tried to send a different file, “file B”, to a different address by dragging file “B” onto mail “B”. Mail “A” with file “A” has not been sent at the time. After writing and formatting Mail “B”, I sent both (actually, I sent 6 mails, A&B, as well as C&D plus two “normal” ones, sending them all off in rather quick succession) via my .Mac account.
Since I was also on the list of addressees, I expected all those mails to show up in my inbox. Instead, only one of them arrived (I don’t remember if that was A or B, to be honest), but it arrived twice. And, (for the sake of explanation, let’s pretend that Mail “B” came back), it had Mail “A”‘s subject line, while mail “A” never seemed to exist. This happened with mail C and D respectively, while one of the other two mails got lost completely, while the other one arrived carrying the lost one’s file, the one I sent it off with was missing. The mails are actually showing up wrong in my Sent folder, as if I sent them away like that.
I know this is a bit complicated by now, that’s why I’m uploading the mails for you in a zip file which I will remove from the server after Dec. 20, 2007. You can see the differing “sent” dates in those files. Here’s the address:
— removed —
And here’s more explanation:
Mail 1a: Was sent 21:55:49, should have been sent only once. Is exact twin of Mail 1b, carries the according subject line and text.
Mail 1b: Was sent 21:55:53, is exact twin of Mail 1a, carries the according subject line and text. (but the mail should have been sent only once at all).
Mail 2: Contains wrong picture file. Was sent off with a blurred image of my cousin, a girl in a red snowboard jacket. The (lost) Mail which contained this picture here (some installation valves for just 19,99!) was sent off to —@—, but never arrived. If you look into my .Mac account’s log files, you’ll find that same picture in some other mail sent in a second try at 22:10:44.
Mail 3a: Was sent 21:55:55, is exact twin of Mail 3b, carries the wrong subject line. Subject line should have been something containing “Toni” and “Lotto” or “Lottozahlen” or “Jackpot”, if I remember correctly.
Mail 3b: Was sent 21:55:56, is exact twin of Mail 3a, carries the wrong subject line as well. Subject line should have been something containing “Toni” and “Lotto” or “Lottozahlen” or “Jackpot”, if I remember correctly. (but the mail should have been sent only once at all).
Completely missing, and therefore neither in my “Sent” box nor in the Zip file I provided, are the following mails:
- Subject “Weihnachten naht” (as in 3a and b), containing two pictures of a christmas market.
- Subject “Das wäre was für Euer Entlüftungsproblem” (or something like it), containing the picture mentioned above with the 5 valves in a yellow paper and clear plastic container.
Phew, I hope you can make something out of all of this. I’d hate to have typed that much feedback just for the dustbin…
Best wishes from Germany,
Julian
December 6th, 2007 at 5:40 am
I can confirm that this happens for me as well on 10.5.1. I do not have mailtags or any other Mail.app extension software installed. I installed Leopard using erase and install so this is not an upgrade issue.
I will file an apple bug as well and link to this post and the forum.
December 6th, 2007 at 7:16 am
Happens to me with and without MailTag. It also happens if I send an attachment using Contextual Menu to e-mail a file ( I think this is a feature of FileBuddy).
One other way to avoid this while it’s being fixed is to make the new mail first and then drag.
December 7th, 2007 at 1:39 pm
Following up. I filed a bug with Apple yesterday on this issue. I heard back from triage today. It is a known Apple issue and my bug was marked as a duplicate of another. I would expect they’ll fix at some point.
–
This is a follow up to Bug ID# 5630858. After further investigation it has been determined that this is a known issue, which is currently being investigated by engineering. This issue has been filed in our bug database under the original Bug ID# 5243377.
–
December 8th, 2007 at 11:28 am
Thanks for posting that.
December 9th, 2007 at 8:19 am
Good, this means it isn’t MailTags after all… One less bug to fix!
December 13th, 2007 at 12:25 am
I also have a similar image problem. I found if you had send an email with an attachment and wish to ‘Send Again’ the email then the attachment does not show up in this new email…one might think. So I add it again. I find that the recipient sees two attachments. I am not sure if my Sent Messages shows both.
I frequently use the resent to send a slightly different version of an email to another person.
December 13th, 2007 at 7:37 am
My problem is similar but not quite what people are here talkiing about.
I don’t have two new-message windows pop open, but after I’ve sent my message (created by dropping attachment into dock icon) I notice there’s still one sitting in my drafts folder. What strange about it is that if I’ve changed the subject line, then there are two messages in the drafts folder – one with the old subject line, one with the new. I just delete them and they go away.
Noticed that behavior last night at home connecting to work’s IMAP server but not today from work. My home and work use different ISPs (one cable, one DSL) so I’m not sure if that’s a factor.
On the plus side they fixed the bug where, if you grabbed an attachment from a windows SMB share and dragged it directly to the dock icon and then try to send the message, you would get an error saying that the message couldn’t be sent using the selected server. I would have to drag it to my desktop and then to the dock icon.
February 15th, 2008 at 4:33 am
I just upgraded to OS X 10.5.2, not via the software update, but via the recommended standalone combo updater (safe boot and so on, there was a howto on the german Macnews site). And… the problem still persists! When I drag a file onto the Mail icon, I get two mail windows again with the attachment in the latter (upper, newer) window. I didn’t try to recreate all the errors descripted above, though.
May 23rd, 2008 at 9:35 am
See if you get any different working if you set your mails to be Rich Text.