Mac OS X’s Mail: can be very dumb at times

Posted by Pierre Igot in: Macintosh
April 24th, 2003 • 10:26 pm

This is not the first time it has happened to me… I tried to send a simple message, and, instead of sending it, Mail got back to me with a dialog warning me that the connection to my regular SMTP server had been rejected and asking me whether I wanted to try again later or try with a different SMTP server. (I have several of them, since I manage a number of different accounts on different servers.)

I cannot use a different SMTP server to send such messages, simply because usually SMTP servers are protected again use by unauthorized third-parties. For example, I can only use the server to send email from my I know SMTP servers are supposed to be able to use some kind of separate authorization mechanism — but in my experience most of the servers I try to use don’t support it properly, at least not as Mail understands it.

Anyway, so I click on “Try later”. The thing is, I have no idea when “later” is going to be, and I want to send the message right away. I know that the problem is not with the SMTP server in question, because it is happily sending other messages. It was just some temporary network weirdness that caused Mail to believe that the SMTP server was rejecting the connection attempt and mark this message as rejected.

Clicking on “Try later” has parked the outgoing message in the “Out” box — which is normally a box where messages are only stored temporarily while they are in the process of getting sent.

So I open the “Out” box and double-click on the parked message to open it. It opens, looks just fine, and the “Send” button is active, so I click on it.

Nothing happens.

I figure that there’s something about this “parked” message that Mail has done that I probably should not interfere with, so I selected it again and instead of clicking on “Send”, I choose “Open as new message” in the “File” menu. This effectively opens a new message that is a duplicate of the parked message. I try to send this “new” message. I get the the same error message about the SMTP server rejecting the connection attempt!

So not only is there something weird in the “parked” message that prevents me from doing anything with it except deleting it — but new messages based on this parked message are “marked” as well!

Grr, grr, and double grr. This is firmly in dodo-head software territory. What happened to user friendliness? This is just atrociously stupid.

The solution is, in fact, to open the “marked” message, SELECT its contents, copy them to the Clipboard, close the message, create a blank new message, re-enter the address of the destination, re-enter the subject line, paste the Clipboard contents INTO the body, and send.

Of course that new message — which is effectively a carbon copy of the doomed message — gets sent just fine using the exact same SMTP server. And the doomed copy still parked in the “Out” box can be trashed now.

Doh, doh, doh, double doh.

There are days when Mail really gets on my nerves.

22 Responses to “Mac OS X’s Mail: can be very dumb at times”

  1. K randle says:

    But what happens when the thing never goes? My second account will not send mail – I have tried every possible config. When I try to change an account’s info, I hit Okay, but when i go back to the prefs, mail has NOT saved the changes to the password, or the port or whatever. You can’t delete the bad outgoing addresses – I HATE this program.

  2. Pierre Igot says:

    You should be able to delete accounts. Some of what you are describing sounds like a corrupted plist file. Try trashing the Mail prefs. Try restarting from scratch. (Back up the “Mail” folder and erase it and the prefs.)

  3. Jaharmi says:

    K – If you’re talking about history of outgoing messages, you can delete those. You have to go to Window > Previous Recipients (in Panther’s Mail; I recall the command being named differently in Jaguar’s Mail). You can then find the bad addresses in the Previous Recipients cache — a history of the addresses that Mail is remembering for you — and delete them from there.

    I have to do this from time to time, based on some oddities for mail delivery in my office.

    I don’t know if this is what you were referring to, but it may help you out.

    I do agree that Mail is not always helpful with outgoing messages, when you’ve encountered sending problems. The messages do tend to go out “sometime,” although I can’t give you any rhyme or reason to when/why. I sometimes quit and relaunch Mail to get them to go (since I don’t like leaving Mail open all the time anyway; I think it develops problems with IMAP UIDs or something over time), and other times I open the message in the “Out” folder and click “Send” to send them now. I do miss the Microsoft Outlook Express / Entourage “Send/Receive Now” feature that sends all pending messages for all accounts.

  4. K randle says:

    The two account thing has been a problem since I started using Mac OsX, a couple of years ago, now – I’ve called AppleCare on it, and they haven’t helped at all – it’s always the other guy’s fault: oh, it’s on NetIdentity’s end – oh, it’s on Apple’s end. I feel like a tennis ball. What really puzzles me is that I can’t even select what kind of mail account it is I’m setting up – the POP on the pull down is grayed out. Is this because of the automatic config thing? It already knows, so it doesn’t need me to tell it? This program is supposed to support more than on POP account at a time – and it will search both accounts for mail, and download. It simply will not allow me to send out on the second account – keeps saying that netidentity refuses the password. I’ve tried starting from scratch. I’ve tried reconfi at NetIdentity – now my husband, on Panther, is having the same problem. First account sends beautifully. Second account simply loads you with error prompts and stupid options. His second account is not the same as mine, so this is not a local problem. I’ll try dumping the prefs, but I have a feeling it’s going to prove to be something deeper. That’s why I come to you mavens – I am an ignorant person, coming to the well for wisdom. I’ll let you know if it works.

  5. Jaharmi says:

    K – I assume you’re on Jaguar Mail, then, since you mention your husband is on Panther.

    Does NetIdentity use and/or require SSL? Do they require user/password login for outgoing mail? Do you know what kinds of password support they have for SMTP (outgoing) mail servers? (There are actually several kinds, and the major ones I’ve used are supported by Apple Mail.)

    Their support site appears to require a login to find out more, so I can’t really help you from here.

    Can you use your ISP’s outgoing mail servers instead? At work, we sometimes have to tell people to do this. Some ISPs in the US are now blocking outgoing mail that goes to SMTP servers off the ISP’s network — this forces you to use the ISP’s servers. Because of these kinds of policies, they will generally accept outgoing mail from any of their customers on their network.

  6. Pierre Igot says:

    K: You can’t change the kind of mail account once it’s been created. If you want to change the kind, you need to delete the account and recreate it. I have about 15 POP accounts in Mail and don’t have any problems with any of them. As for why messages don’t get sent, unfortunately, it can be a tricky issue, involving both Mail and the SMTP server of your provider. You need to try with and without authentication.

  7. Pierre Igot says:

    The different “kinds” of authentication appear in the pop-up menu in the “Advanced” section for your account. The most common one is “Password” (the first one), and it’s different from SSL, i.e. you shouldn’t check the “SSL” box unless your provider specifically instructs you to do so. The authentication method selected works without the SSL box (which changes the port used for the authentication).

    I agree that the interface for all this is not clear to the uninitiated. I am not very familiar with all these technologies myself and just learned what worked through trial and error. Not always pleasant, I must say.

    You should be able to change all the settings in your Mail preferences dialog. They are user-specific and do not require an administrator’s password. The “Account Type” is the only one you cannot change once you’ve created the account.

    Hope this helps!

  8. K randle says:

    NetIdentity, up until a week ago, did not seem to require password authentication. For the last year, when the mood possessed me, I tried connecting with password, without password – until Mail stopped saving the changes I made in the prefs. I’d select the authentication, list the password info, save – then the next time I’d check it, all would have disappeared. Now they do require authentification, and I’m going to have to figure that one out, somehow. They so not support SSL. At least, they didn’t – maybe I’d better ask that questions. I will also check up on the passwords for SMTP, as I had no idea there were “kinds.” The depth of my ignorance frightens even me.

    I can’t use the ISP outgoing either. We tried that – we’re on comcast. (our form of ATT). But maybe it would work if I knew the right password stuff – maybe that’s the problem.. I have tried setting up the account with my own URL’s outgoing info as- but that hasn’t worked either.

    I figured you couldn’t change the account (other than the menu options in prefs) since I can’t get inside Jaguar to find the files. I mean, I could try – but this is probably why the computer has been so stable: me barred from playing with the grown up toys. Okay, I will try these things, too. And if I have any hair left – or any energy – I’ll report back.

  9. K randle says:

    Okay. Now I feel like an idiot. In a fit of simplicity, I did what someone up there recommended, deleted the 2nd server, and then re-entered the whole bunch of info. Mind you, I have done this before. I have a list of outgoing servers a yard long. but for some reason, tonight, it worked. I can go out of it. i can come into it. Everything works. Yes – but for how long? I recall that it worked for me once before – for about 10 minutes. Licking stamps was easier.


  10. K randle says:

    Pierre – what is a plist file? I am sitting here thinking about throwing away the prefs – I hesitate because I don’t want to go through the agony of having to put in all the rules again. When you say back-up the mail folder – you mean the individual account folders? If I were to delete an account, the deletion would take all my past messages with it, would it not? If I back it up, make a copy, could I rescue those messages, none of which I am happy about losing just now? I do not, by the way, find any mail prefs anywhere – I am looking in my user library. You are the maven – lend wisdom –


  11. Pierre Igot says:

    K – no need to feel like an “idiot”. Too many things in today’s computers — including the Macintosh — are flaky and it’s not at all unusual for things to start working whereas they wouldn’t work previously.

    A plist file is the preferred format for preference files in Mac OS X. They are all located in the “Preferences” folder inside your home library folder. For example, the pref file for Mail is “”.

    Sometimes these files do contain valuable information. In the case of Mail, however, most of the important information, including your rules, is in the “Mail” folder in your home library folder. So you won’t lose your rules by trashing the plist file. You will only lose things like the position and status of your main Mail Viewer window, the position and visibility of your Activity Viewer, the columns settings for viewing mail, etc. It’s a bit of a pain to restore these settings, but most of the important stuff is in the “Mail” folder.

  12. K randle says:

    Pierre – I think you are wonderful.

    And it still works this morning – after mousing with the thing for a year and a half…

    Go figure.


  13. Eric says:

    I’m also having trouble with Mail and NetIdentity. I can access my .mac acct. w/Mail, but not my NetIdentity acct. Tried trashing the prefs, but that also removed most of my emails I’d saved as well (fortunately I kept the file in the trash and could replace it.

    This has happened before but always has resolved itself after a few minutes; now I haven’t been able ot access my NetIdentity mail all day, so have had to reroute it.

    Anyone have any ideas?


  14. Kristen Randle says:

    NetIdentity has changed its protocols in the last week. You have to reconfigure your account to match their new set-up. You should have been getting emails to this effect from them – but then, how would you fish them out with all those lovely virus posts people have been sending along? Go to netID and log on to your account – they’ll have the new protocols explained there.

  15. Eric says:

    Thanks, I’m aware of this. However, NetIdentity specifically states NOT to change Mail settings until 2/2/04.

    Just in case they were wrong, I changed the settings, and that also didn’t work.

  16. Kristen Randle says:

    Hmmmm. I would still think the problem is on their end. By re-routing, I’m guessing you forwarded your netID to the Mac address. I’d give it a couple of days, and if you can’t get the account to work then, let me know and we’ll work on it together. I don’t know if my account is working – I forward, and it all happens so fast – wait, let me check my activity window. As far as I could see, I was connecting to NetID okay – the last little flurry of activity happened so fast, though, I couldn’t really tell. I cleared up my problem (my over-a-year problem) by re-establishing the account, which I could do, as I do forward and had nothing stored in my NetID file. I don’t know why it worked that time; I’d tried it many a time before. I guess you should probably change things back the way they were, see if anything happens, then wait till the 2nd. They did have rather dire warnings about changing early. their support has been really lame, by the way. It’s always somebody else’s fault.

  17. Eric says:

    After 24 hours of Mail not working, this morning it magically started again. This has happened before, but only for a few hours, not a full day. I received a note from NetIdentity today with no explanation of why, only a question as to what was going on.

    I’m stumped.

  18. Kristen Randle says:

    I’m with you. It strikes me that this is all a lot like life in general – one day, things don’t work the same anymore. You’re eating the same, and then suddenly, you’re gaining weight. then it swings back – why? Why indeed. Glad it’s working. Sorry I wasn’t more help.

  19. Eric says:

    one last point–I think it’s definitely NetIdentity’s problem. I remember now that I opened up Entourage, and I had the same problem–Entourage accessed my .Mac acct’. but couldn’t open NetIdentity’s. Got an error msg something like “authorization denied.”

  20. Pierre Igot says:

    OK, if you guys have any more issues with NetIdentity, I’d appreciate it if you could continue this conversation in private. I don’t think it’s of much interest to Betalogue readers in general. Thanks for understanding :).

  21. Kristen Randle says:

    Thanks for your help, Pierre. I really appreciated it. merci bein. bon Journey.

  22. tony harris says:

    many many thanks – i thought i was the only one going mad – so did everyone else I can now print off your list in font50 and give it to everyone who tells me to forget apple and get on the real hot lines I must admit it is a beast for me, thats is because untill this week I guessed most things – now I am reading HELP and lists like yours many tas amh

Leave a Reply

Comments are closed.