Mac OS X Mail Tip: Sending unsendable messages

Posted by Pierre Igot in: Macintosh
September 4th, 2003 • 6:20 pm

If you use Mail with a modem connection, you’ve probably encountered this situation from time to time. You write a message in Mail and want to send it, but it just so happens that your limited bandwidth is being monopolized by a downloading process somewhere in another application (Safari, FTP application, etc.).

When you click on “Send”, Mail gets confused about the lack of bandwidth available and thinks that it is the SMTP server for your email account that is not responding. It then suggests two options: “Send Later” and try sending with an different SMTP server.

The other option is rather puzzling, in so far as there are authorization issues that often prevent you from sending email from account 1 via the SMTP server for account 2. Sometimes it can be done, but often times it cannot — and Mail doesn’t seem to be too clever about determining which SMTP servers might be willing to cooperate with the email account that you’ve used to compose the message you cannot send. It effectively — as far as I can tell — choose another SMTP server at random among all the ones that are available. Fortunately, it lets you change its default choice to something else (depending on how many SMTP servers you have available), but even you might not be familiar enough with the security features of each of these SMTP servers to determine which one might work with the currently queued and unsendable message.

So you click on “Send Later”, which is probably the wiser thing to do. But now, what does “later” mean here? There’s no indication of it in Mail’s interface. The unsent message just sits there in the “Out” box doing nothing. If you open the message and click on the “Send” button again, it doesn’t move. It is still, presumably, waiting for the “later” period of time to elapse, based on its internal (and invisible) time keeping.

What to do then? You don’t want to entrust Mail with finally sending the message whenever it decides that “later” is now. You want to send the message now yourself. What you can do is the following: Interrupt your downloading process or whatever is monopolizing your available bandwidth. Go back to Mail, go to “Out”, open the unsent message so that the “Send” button in its toolbar is readily available. Now, leaving this message window open, ask Mail to CHECK your email. While Mail is checking your email, click on the “Send” button in the unsent message window.

Now the message should be sent right away. I haven’t used this trick often enough to ensure that it is 100% reliable. But in the few times when I have had to deal with an unsent message and the “Select another SMTP server” dialog, clicking on “Send Later” and then doing this has worked.

There’s probably something in the connection established with your email servers when checking mail that also enables Mail to communicate with the servers to send unsent email messages.

It’s not exactly elegant, but until Apple fixes Mail (and it might still take a long time, by the looks of it), it should help.

6 Responses to “Mac OS X Mail Tip: Sending unsendable messages”

  1. Ortwin Zillgen says:

    that’s the way Mail works :-) even with semi-permanent DSL-connection.
    I’ve given up, sending any mail without first asking Mail to fetch the incoming mail.
    If it’s sending one, later is over and others will be send too.

  2. Pierre Igot says:

    “works” is a nice euphemism :). That’s the way that Mail convolutedly manages to get sending mail to work. I did hear reports that the problem could also occur with DSL connections. But why do you ever encounter the issue if you have enough bandwidth? Or is Mail poor at handling bandwidth even with broadband access?

    I USUALLY am able to send mail without checking my incoming mail at the same time. The problem only occurs when I don’t have enough bandwidth available for Mail and it gets thorny about it.

  3. Dan Farrell Davis says:

    I don’t use Mail very much, but I have seen this exact problem many times. My impression also is that it is related to connectivity, but it is only an impression. Many Mac (Mail, Entourage, etc.) users have SMTP problems with various ISPs, mostly cable ISPs in my experience. And these cable problems are related to cable modems based upon my research. Some sending issues are related to attachments. Today, for example, Cox Cable status page ( says, “Customers with Motorola SB5100 cable modems may experience problems sending email attachment larger than 20kb.”

    So it is not completely a Mail issue.

    With all the SMTP changes being made by ISPs, you’re lucky if your problems have been so few.

  4. Pierre Igot says:

    Well, I tend to speak from the perspective of the average user, who really doesn’t give a hoot about SMTP servers and all that jazz, and just wants to be able to send email messages without having to fiddle with settings all the time. Clearly Apple still has some work to do here. Whether it’s a flaw in Mail or poor support from the ISPs, the user doesn’t care. It needs to work transparently for him.

    I don’t think not having too many problems is being “lucky”. It should be the normal situation.

  5. L Kimbell says:

    For me this is definitely an OS X Mail problem. I was using Entourage happily for a few months with a 56k modem and decided to switch to Mail. I have had the experience described above of being told the SMTP server is not responding, even when I have no other internet clients running and presumably no bandwidth issues.

  6. Pierre Igot says:

    Well, with OS X, on a modem connection, there is always the potential for bandwidth issues. I recommend installing a utility such as MenuMeters, which lets your monitor more closely what’s going on with your modem connection.

    That being said, things seem to have improved significantly with Panther’s Mail in the SMTP department. Are you still using Jaguar’s Mail or Panther’s?

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