Home Forums Networks & Cross-Platform Networking Infuriating Mail.app

In 10.5.7, Mail.app asked for permission to access my keychain the first time I launched it after restarting and functioned as expected after I entered my password, but since I upgraded to 10.6.4 it asks for my password for each e-mail account, refuses to remember them in my keychain despite my checking the box, and makes me enter each password twice before it picks up mail. (I deleted my passwords from my keychain and tried re-entering them manually, but to no avail.)

Trying to send mail elicits similar behavior, despite the fact that my passwords are still stored in my keychain. (Mail.app does ask for permission to access my keychain and then ignores the stored passwords.)

Aaargh!!!

Has anybody else run into this issue?

Thanks.

(I think I need to trash my upgraded Leopard volume and do a new clean install of SL.)

Update... It's checking the "Remember..." box that causes the second password request; if I don't check it on the first request my new mail is picked up.

Also, Mail seems to be the only app having keychain issues; Safari works as expected.

Read If Mail keeps asking for your keychain password. It might help.

sounds like your keychain may not be unlocked. open keychain access in the utilities folder, and see if the big gold lock s unlocked.

I'm OS 10.6.4 and Mail 4.3

My Mail acted peculiarly a few days ago. For no explicable reason it a dialogue box would pop up saying that the mail server did not recognize my password, which it stated as being the part of my address that is before @.

That has never been my password and I have no idea why it might think it was.

Because it was so strange (and because I am a bit paranoid about passwords being hijacked) I contacted my ISP but they said it was nothing to do with them.

Therefore I re-entered my password, using Mail preferences. Mail would work once or twice and then I'd get the dialogue box again. Therefore I used the dialogue box to re-enter the password, including the instruction to Remember in My Keychain.

This continued a few more times then, just as inexplicably as it all started, it stopped. Things have been normal since.

ryck

Thanks, Jon, but that's not my answer. (See my response to V1.)

I can't help you with that one, ryck; it's nothing I've ever run across.

Edit: On thinking, your issue reminds me of an ISP glitch I ran into once, and its having corrected itself is confirmation, in my head, anyhow, that it was an ISP glitch.

Good try, V1, but it's a no-go.

First, I was ahead of myself saying that my keychain functions as expected in Safari; experimentation has revealed that it doesn't:

• I'm unable to add new items to it; Safari asks for access, and even after I enter my password they're not added.
• I deleted the Safari item from it, but I'm still unable to delete anything from Safari > AutoFill.

I ran Keychain First Aid which repaired something...no joy.

I created a new keychain and painfully moved all my items into it...no joy.

Keychain Access seems to have lost contact with the rest of OS X, at this point I'm convinced that it is corrupted, and that, along with the other issues I've run into since I upgraded (by the default upgrade procedure) to SL, has convinced me to do an erase and install and start all over again.

Booo!!!

Edit: As a stopgap until I'm ready to reinstall SL I reinstalled Keychain Access with Pacifist...no joy.

Before you resort to the E & I, have you tried if (re)running the Mac OS X v10.6.4 Combo Updater helps?

Well, I'll be darned!!!

I held out virtually no hope after reinstalling the app didn't turn the trick, but rerunning the 10.6.4 Combo was, indeed, the answer, and I'm embarrassed about not having thought of it myself. (I wonder how many people are like me in being [more or less] knowledgeable when on-line and turning into complete imbeciles when confronted with their own issues?)

Drinks are on me next time your in NYC.

Many, many thanks for saving me from the E & I.

it's also worth noting that an archive and install would likely have fixed it if a combo updater fixed it.

Something went wrong when I ran the Mac OS X 10.6.4 Combo Updater the first time, on June 21.

If I recall correctly, every other running of a combo updater, which replaces thousands of files, overwhelmed the fsevents database used by Time Machine, which forces Time Machine to perform a deep traversal the next time it runs. That simply did not happen when I ran the 10.6.4 Combo Updater on June 21. The next Time Machine backup was suspiciously brief.

I looked at the modification dates of two files that are in application-specific folders within /Users/user_name/Library/Application Support, the Apple Address Book data file and the database used by Yojimbo. In the Time Machine backups, both files still had modification dates of June 21, even in the June 25 backup. The applications were not running when Time Machine made its backups.

I saw Console entries that made little sense:

6/25/10 10:30:48 AM com.apple.backupd[87631] Starting standard backup
6/25/10 10:30:48 AM com.apple.backupd[87631] Backing up to: /Volumes/H_G_Wells/Backups.backupdb
6/25/10 10:30:48 AM com.apple.backupd[87631] No pre-backup thinning needed: 665.5 MB requested (including padding), 400.91 GB available
6/25/10 10:30:50 AM com.apple.backupd[87631] Copied 28 files (93 bytes) from volume MacBook_Pro_C2D.
6/25/10 10:30:50 AM com.apple.backupd[87631] Starting post-backup thinning
6/25/10 10:30:50 AM com.apple.backupd[87631] No post-back up thinning needed: no expired backups exist
6/25/10 10:30:50 AM com.apple.backupd[87631] Backup completed successfully.

If I added a new file to the root directory, Time Machine would back it up properly, and if I modified the test file, the new version would appear in the next backup. But database files deeper in the file hierarchy were not being backed up.

To be completely certain that Time Machine was malfunctioning, I did a full restore to a bootable external FireWire drive, and booted from the restored system. The Address Book and Yojimbo databases showed no changes after June 21.

Reformatting the drive used by Time Machine, giving it a new partition map and a new Mac OS Extended (journaled) volume did not solve the problem.

After reinstalling the 10.6.4 Combo Updater, a deep traversal was performed:

6/25/10 2:15:46 PM com.apple.backupd[189] Node requires deep traversal:/ reason:must scan subdirs|

The process took more than an hour, but Time Machine has worked properly since (as far as I can tell). I urge you to make sure that Time Machine is not faking it on your Macintosh.

Do not feel bad about this. I have to pretend to be MicroMatTech3 when I have my own computer problems, and to remind myself that being helpful to others does not grant one an exemption from having problems of one’s own.

Hmmm... Doesn't an A & I in SL leave you with the same updated version of OS X with which you started, in which case you'd still have to rerun the Combo if it's what caused the issue in the first place?

Sounds like a cumbersome last resort?

(I've had abysmal luck with A & I, so when it seems to be the thing to do I opt for erase and install which leaves my installation pristine and snappier than it had been.)

Thanks for that, MM T3, but I don't use Time Machine.

Thanks!

That makes me feel a bit better.

OFF-TOPIC: huge "mistake" there. [seriously, Time Machine is truly one of the best features to hit Mac OSX in a while.]

Better, even, than SnapBack?

Seriously, though... While I realize that Time Machine could someday save me from an erase and install (I disdain A & I.)...

• Virtually everything important on my deuced Mac(hina) is on a separate partition from OSX.
• My most recent clone will be 99% up to date even if it's a full month (my max "between" time) old.
• My physical setup just plain doesn't lend itself to keeping an external HD attached to my laptop.

My purposes are as well served by backing up my home folder (which is all of 110Mb, 80Mb excluding Microsoft and Firefox profiles, at the moment) if something important in it changes as they'd be by using TM.

And, finally, the thought of having to do a highly unlikely erase and install doesn't phase me, because...

• I'm set up for really easy re-installation.
• I know my Mac will benefit from the experience and be happier, i.e. more responsive, afterwards.

That said, I'll admit that I've got a spare 200Gb partition on my internal HD which, although I realize it will not be an ideal situation, I'm thinking of using for TM. (I doubt that even that much space space will be necessary for backing up a 6Gb volume.)

Now this is curious...

A coupl'a hours ago I discovered that my legendary powers of observation ( ) had apparently failed me, yet again, when I booted into my Leopard volume and discovered that my Mail issue was not new to my upgraded SL volume, but a carryover.

As with my SL volume, rerunning the Combo Updater (10.5.7 in this instance) cured the problem, but I'm left wondering why, if the problem existed before I upgraded, the upgrade, itself, and subsequent initial running of the 10.6.4 Combo didn't cure it in the first place?

Some leftovers from 10.5.7 like corrupted database, etc?
BTW, the SL does A&I by default when you want to reinstall system software. To do E&I, you need to instruct it manually. Therefore, it is not that "painful" as before.

1. Perhaps, even likely, but that doesn't explain why the upgrade and initial running of the 10.6.4 Combo didn't clear up the issue. Why did it take that plus a second running of the Combo to turn the trick?

2. The "less painful" part seems to be no more than that we can now A & I without booting from our install discs; the more painful part, on the other hand, is that we can apparently not A & I to an earlier version of OS X than that from which we started, rather we must do an erase and install and update from there to accomplish that.

Update...

The last time I ran into this recurring issue (several months ago) I realized that I had just edited the "Secure Note" I kept in my keychain.

The note is only about 8k and wouldn't figure to be an issue, but it seems to have been at the root of my assorted keychain problems, because deleting it (and re-running the latest Combo) has apparently stabilized things.

Damn! False alarm...

I booted into my Leopard volume to check something, and when I booted back into my Snow Leopard volume I found that Mail.app had lost its connection to Keychain Access...again.

After trashing ~/Library/Preferences/com.apple.keychainaccess.plist with no attendant joy I reran the 10.6.6 Combo for the umpteenth time, and all is well again.

(Mail.app in my L volume is suffering from the same ailment I just cured in my SL volume...10.5.6 Combo time. Aaargh!)