Broken hyperlinks in Apple Mail
While I love Apple Mail, one thing in particular about it bugs me; it has a habit of breaking hyperlinks so that recipients of my emails can’t just click on them the way they should be able to. When I add “http://forums.whirlpool.net.au/forum-threads.cfm?f=38” to an email, people using other mail clients often receive it as “http://forums.whirlpool. au/forum-threads.cfm?f=38″ and that’s frustrating for everyone. One PC-minded friend of mine has recently declared that he is “just going to give up” on anything I send!
It’s easy to see how this happens with Apple Mail. At least David Duff posting on MacInTouch has an answer:
Other posters correctly point out problems with sending url’s in mail…when sending, Mail.app uses a “Content-Type: text/plain;” with the option “format=flowed”, which seems to be fairly standard. It also uses the option “delsp=yes”. the semantics of the delsp option are that if delsp=yes, then the space at the end of the line should be removed when the lines are joined together into paragraphs.
When doing “normal” line wrapping between words, where the space should be present, Mail.app ends the line with two spaces. When wrapping a line with a URL, where the space should not be present, Mail.app uses a single space. Thus, it should be possible, in theory, to correctly reconstruct the URL.
Unfortunately, this doesn’t work. At least not when sending mail among the most popular two mail clients on the Mac platform (namely Mail.app and Microsoft entourage). the problem may be that the delsp option is a fairly new (added between RFC2646 and RFC3676) and not yet widely adopted.
That’s the explanation, but what’s the solution? Sometimes Apple can be too innovative, and here is a perfect example! While we are waiting around for the rest of the internet to catch up to the delsp option, there must be a way to fix this? Anyone know? Do you?
Tags: annoyance, Apple Mail, broken hyperlinks, bug, line wrapping, mail.app, URLsRelated posts

August 6th, 2005 at 9:10 am
I don’t know that answer either.
Perhaps you just have to wait for the rest of the world to catch up to Apple’s implementation of the delsp standard.
August 21st, 2005 at 8:00 am
[...] One way to solve the broken hyperlinks annoyance in Apple Mail 2.0 is to make your URLs and hyperlinks so short that they can’t break. A free service on the web called TinyURL can help you do this. Here’s how it works: [...]
October 29th, 2005 at 3:39 am
This problem extends beyond just URLs. I send a message from Mail.app, and my PC friend quotes it in his reply. Two spaces appear between words sporadically in the quoted text. The two spaces forever pollute mailing list archives and all sorts of discussion databases which nowadays are hooked into email. What a mess!
There has to be some hidden preference for Apple Mail to use the “old fashioned” (last-year) method of formatting email without this “delsp” thing which will probably never catch on, despite Apple being technically correct. Hmmmmm.
I just did some tests, looking at raw email text, and what Apple is doing is pretty slick, technically speaking. What a pickle.
Paul
October 29th, 2005 at 8:44 am
Yes, it is a pickle. Apple is following the RFC standard on this, but no one else is. Which in a way makes the standard non-standard!
I have often wondered if I could modify the Content-Type header to remove the delsp=yes tag, but haven’t actually done it.
January 3rd, 2006 at 9:46 am
For what it’s worth, I filed a bug report with Apple.
January 3rd, 2006 at 10:25 am
Hi Bill. Good idea, although I bet that since delsp=yes is now part of the RFC standard (although no one else supports it), Apple will not think it is a bug.
They will think that everyone else has a bug! (Theoretically correct, but practically frustrating!).
February 2nd, 2006 at 4:53 am
The temporary solution for the hyperlink problem is for the sender to drag-select the text of the hyperlink, copy it to the clipboard, then right-click (Ctrl-click) and select “Edit Link…” and paste the link in the dialog box. Not elegant, and a PITA, but at least it makes links clickable for our PC (and webmail, and Entourage…) friends.
March 1st, 2006 at 1:37 am
i would love to do what Josh suggests but couldn’t get it to work. Does this work in Apple Mail 1.3.11?
March 1st, 2006 at 7:58 pm
Sem: I can’t really remember now, but MacInTouch’s review of Mail 2.0 suggests that the “Add Hyperlink…” feature was a new thing with Tiger:
“Aside from the addition of an “Add Hyperlink?¢‚Ǩ¬¶” menu item, Mail’s composition window offers no better text or layout controls than 10.0’s Mail did in 2001.”
http://www.macintouch.com/tigerreview/tiger1e.html
March 8th, 2006 at 1:40 am
I always put URLs in a line on their own. That way I can guarantee that, as long as they are shorter than 78 characters, they won’t be wrapped.
June 20th, 2006 at 7:57 am
The Add Hyperlink… does NOT work at all, same problem. This really sucks and is totally embarassing in terms of talking with Open Source and even windowz fools who can do this without any problem.
Apple needs to QA their software much better than this.
June 20th, 2006 at 8:02 am
John, what happens when - with a message set to Rich Text Format - you block some text in the Compose window and then select “Add Hyperlink”?
July 13th, 2006 at 8:13 am
This looks like a bug unfortunately.
http://blogs.sun.com/roller/page/simons?entry=apple_spaces_out
The spec notes that spaces should not be inserted into URLs by the generating agent. Mail.app ignores this command.
April 6th, 2007 at 7:44 am
Can anyone explain why outgoing mail needs to be post-formatted at all? The display of emails in different sized windows should be handled on the fly, without changing the original text at all.
If a simple word processor like TextEdit is smart enough to wrap text without adding a hard carriage return or a space, why can’t email clients do the same thing? This has bugged me since the beginning of email.
April 6th, 2007 at 3:30 pm
Apple doesn’t do things badly for once here. They implement the specification correctly. The irony is that other implementations don’t and it’s why it is annoying for others. Unfortunately.
May 17th, 2007 at 1:09 am
Apple *does* do things badly here. The spec (RFC 3676) says
“Regardless of which technique is used, a generating agent SHOULD NOT insert a space in an unnatural location, such as into a word (a sequence of printable characters, not containing spaces, in a language/coded character set in which spaces are common). If faced with such a word which exceeds 78 characters (but less than 998 characters, the [SMTP] limit on line length), the agent SHOULD send the word as is and exceed the 78-character limit on line length.”
In other words, as long as your URLs are shorter than 998 chars, your mail client SHOULD NOT be touching them.
May 25th, 2007 at 2:59 am
> Can anyone explain why outgoing mail needs to be post-formatted at all?
Because MIME/SMTP protocols are very, very old, have all kinds of weird limitations and there are a lot of badly written mail servers and clients out there.
FIY Opera’s e-mail client (AKA “M2″) does support delsp=yes standard and I think Mozilla’s Thunderbird is at least trying to (but often wraps signature delimiter when it shouldn’t)