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David, Mac Support Specialist
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My Ical keeps asking for passwords, repeatedly on the same

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My Ical keeps asking for passwords, repeatedly on the same account. This started when my email was hacked and I did a full reformat and reinstall of the OS (10.7.5). It worked OK for a couple of days and is now asking for the pw constantly again. Help?
Hi, my name is XXXXX XXXXX I will do whatever I possibly can to help answer your questions.

Please open iCal, then click the iCal menu on the menu bar in the top left, and click Preferences.

Click the Account tab. Please list what accounts you see.

Customer: replied 4 years ago., icloud,


The next question is whether you want to keep any of those accounts. Do you need any of those accounts syncing up with iCal?

Customer: replied 4 years ago.

Yes, I need whatever/whichever of these will make my Ical sync on my Iphone and on my laptop. These have all been set up since I reformatted and reinstalled the os. I also didn't import any of the old emails or old email settings, since I feared I would import some of the old settings that were causing this problem before.


You can do that with one calendar, I recommend using just iCloud.

Before removing the other accounts you should check what calendar items are in.

You can quickly tell by the colour. If you are not sure, click and item, then click Edit -> Get Info.

You can check which is the default calendar in Preferences. Click iCal -> Preferences and you should see which is the default.

When you are sure you have all items you need in iCloud, go ahead and delete the other two accounts.

Then restart the mac and check if you get asked for password. If you still are then we can check the login keychain etc, for the iCloud account.

Please get back to me if there are any problems.

Customer: replied 4 years ago.

Do you mean I should physically remove the Ical accounts listed, except for the Icloud?


Why did Mail ask me if I wanted to set up calendars (and ichat) for individual email accounts when I set them up? I unchecked Ichat because I don't use it, but I left the other two options checked, one of which was Calendar. I assume that is why I have 3 accounts set up now in Ical preferences. No problem deleting two of them and leaving ICloud, but I don't understand why I was having the problem...was it 'getting confused' since I had it checking for 3 different accounts/calendars?


I'm restarting now and will get back to you if I have further problems. Does this also cause popup windows that tell me an item moved to the trash can't be deleted 'because the connection to the yahoo server timed out', or is that a non-related problem?


I think the error from Yahoo! is because Bell South uses yahoo! for their email and calendar servers. If it keeps happening, we can investigate it further, but I think it will not happen again when the Bell South calendars removed.

Yes, remove the Bell South accounts, in iCal.

When setting up an email account, Mail asks you because it can manage calendars. You can use multiple calendars, but this brings on multiple complexity, and syncing issues. Passwords can just be one of of the potential issues, so sticking with one calendar for sync is much easier.

Let me know how it goes, and if there are any new issues.


David and 6 other Mac Specialists are ready to help you
Customer: replied 4 years ago.

Ok, I appreciate the explanation. I have another question that I think is related to this question, or at least may be caused by the same situation but I am not sure. If it's an entirely different issue I understand..I am not trying to 'get something for nothing'. The issues did start at the same time however....after I had reformatted, reinstalled os, etc. (and they were both occurring before the reformat, etc, and are the reason why I did all that to try and fix the issue). They all 4 have to do with Mail. Four issues...1) When I move emails to the trash, about half the time I am getting a message within a minute or so that says, "The message XXXXXX could not be moved to the mailbox "Trash". The connection to the server '' on port 993 timed out." and 2) Mail continues to ask for the pw for certain email addresses, no matter how many times I put it in, ask it to remember it & to add it to keychain. and 3) 'Sent' emails are staying in the 'Draft' folder after they are actually sent, and 4) new emails in one of the email account Inboxes are never marked as Unread. They show up in the box as already read. I can change them to 'Read', or to 'Unread', but when they show up initially they show as already having been read.


Again, i understand if this is a different question/issue than what I asked initially, but the problems certainly seem to be related to me. Thx.

HI Barry,

That's absolutely fine. Don't worry, these are all in some way pertaining to in Mac OS X.

How many email accounts are in Mail. Go to Mail -> Preferences -> Accounts to check.

Which ones are IMAP, and which are POP?

Do you have a backup of your data? For example do you use Time Machine?

Thanks in advance,
Customer: replied 4 years ago.

There are 4, and all are IMAP. None are POP.


I have used TM for a long time, but when I reformatted and reinstalled I purposely didn't restore anything from TM in my Mail accounts fearing I would 'restore' this problem I explained to you above (repeatedly asking for pw's). This problem (in mail and calendars) began a few months ago after my main email at&t ( email was hacked. I tried to fix it inside Keychain, but even though I am a long time (1986) mac user and am pretty knowledgeable, Keychain issues were something I had never dealt with. I'm sure I did something having the account reset by bellsouth I did my reformat (using Disk Genius) and reinstall of 10.7.5...and I just entered my email accounts anew...and allowed them to begin with current emails. I would like to have my old emails back again (the actual emails I mean, sent and received) but again, was fearful of restoring from TM and 'bringing back' the old problems with asking for pw repeatedly. I have not used TM since my reform/reinstall, but I need to begin doing so again soon.


I would like you to begin a new Time Machine backup, before we do the steps I have for the issues. The steps are to rebuild mailboxes, and there is a small chance the mailboxes will be corrupted by this process if they are somehow already faulty beyond repair.

There is no need to erase your old Time Machine backup. When the issues is resolved, Mail works with Time Machine to restore hand picked emails. Mail is one of the applications that works with Time Machine in such a way that you can browse back in time, and you can select items to restore. I would prefer to do this after rebuilding mailboxes, after fixing the issues.

Can you begin a new Time Machine backup of your new system. Let me know when it is backed up, and you are ready, or if you have any questions.

Customer: replied 4 years ago.

Pretty sure I know the answer to this, but if i do a new TM backup now, it will copy what is currently on my newly reformatted drive, and the older backups that are on the external drive will stay in place on that external drive, right?


Yes, the old Time Machine backup will still exist as a different disk image. You can access it later.

Customer: replied 4 years ago.

When I went to do the new TM backup, I had about 7 backups saved on my external disk (the last time I looked at it). This time, TM could not complete the backup because it said I need over 100 gig to do so, and there is only 54 gig available. In addition to that, it has deleted all but the last backup that was on the external, I'm assuming to make room for the new one. Thus, I cannot complete a backup. I've gone all through the preferences, and looked online, and i cannot figure out why this is happening. When I do an info lookup on the drive it says I only have about 52 gig avail, but when I open the drive and check the files that are on it, I am using less than 45 gig of the available space of the drive, which is 320 gig. If you can't help me with this, I'll just move forward with your help with the original problem without backing up. Thanks.


Sorry for the delay, I had been traveling and had no access to JA.

The space discrepancy could be simply explained by items remaining in Trash.

When an item on an external drive is moved to the Trash, it's not i mediately deleted in case you want to recover it from the Trash. A file on an internal drive is moved to the Trash folder on the internal drive, but a file on an external drive is moved to a hidden Trash folder on the external drive. The file does not appear on the external drive but is still taking up space on the external drive. It will take up that space until the Trash is emptied.

Check what you have in Trash, and if its OK go ahead and empty the Trash. Next check the available space.

If this was not the reason for the space discrepancy then it will be one of a few other possibilities, such as a damaged disk image file. We can investigate those possibilities if emptying the Trash does not resolve the problem.

You can also make your Time Machine backup smaller by excluding System Files and Applications from the backup. You can see how this is done in the section on excluding items from backup in this article:

Let me know how this goes and any new questions that arise.

Best regards,
Customer: replied 4 years ago.

Thanks....I had already tried emptying the trash..even did it as Secure Empty Trash. Made no difference in the size avail on the external. I unplugged it...plugged it back in, checked trash again (empty) and still the same result. Emptied while connected to external, no difference. I knew how to exclude items from backup, and tried that also, but still it says there is not enough room to backup. (Drive is 320 gig, says avail is about 52 gig). 'Mail" app continues acting up. WAY too slow to download new mails, one mailbox (main one) still doesn't show unread mail as unread but as read immediately when it is received (before I even look at it), and continually tells me that it can't delete messages because the server is timing out. i've used Mail for a long time and have never seen these issues.

Hi Barry,

How many items are on the external drive now?

List each one, and click on it then File -> Get Info and list the size of each one.

Then check the capacity and remaining and let me know those figures also.

Kind regards,
Customer: replied 4 years ago.

First….Before I reformatted my hard drive, I had two partitions on my internal drive. They were named 'Dad's Macbook Drive', and 'Lion'. I had 10.6.8 on the first one and 10.7.5 on the second one. They were equal in size. I only used 10.6.8 for Quicken and Photoshop. I did all mail, calendars, etc on the Lion drive running 10.7.5.


Install Mac OSX 4.3 meg
Backups.backupdb 41.29 gig

> Inside Backups.backupdb:

Barry C Smith's Macbook 40.81 gig

>> Inside Barry C Smith's Macbook

2013-08-19-163547- 40.81 gig
Alias to folder> Latest 17 k

>>> Inside 2013-08-19-163547

Dads Macbook Drive 9.1 gig
Lion 31.8 gig

>>> Inside Alias to folder> Latest

Dads Macbook Drive 9.1 gig
Lion 31.8 gig

Capacity: 319 gig
Available: 52.84 gig


The two volumes and two corresponding backups make this a bit more confusing.

Is there anything in the backups that you don't have on the existing volumes on the MacBook?

If not then cast off the old backups, and start fresh. That would be the cleanest and simplest way to move ahead.

I would wipe the external drive, also recreating the partition in the process, and then start new backups of both internal volumes. Excluding the System on each to save space.

Is this something that you can do?

Customer: replied 4 years ago.

Is there anything in the backups that you don't have on the existing volumes on the MacBook?


Yes, everything on the external backup are things that don't exist on the volumes of the Macbook. I have not done any backups since the reformat, reinstall because the external would not hold a backup.


It appears to me that I have two exact copies of the existing backup on the called '2013-08-19-163547- 40.81 gig', and one that I get to when I click the alias called, 'Latest'. Perhaps I am wrong and the alias is just pointing to the first file I just mentioned?


That fear is keeping me from deleting anything on the backup drive in order to move forward and get the problem fixed. I hate being motivated by fear. Maybe I need to get another drive to move all the backkup drive contents to, and then I can reformat and repartition my backup drive in order to move forward? I have another Mac with sufficient space to do this on my network...


Sorry about that, I wasn't sure if you had recovered everything.

You have two systems installed on two partitions. I am thinking now that one is backing up, and that it also backs up the other volume. Then the other system is possibly also backing itself up, and the opposite volume. When setting up the Time Machine backups again, I would exclude the second volume from the backup scheme on both systems, and let them just back up their own system.

There is something wrong with the structure of the external drive. When you mention other Macs on a network, do you also have PC's? I know there is a problem that Windows creates when it accesses a Time Machine backup volume, and that may have caused the space problem. There is no way to fix it other than erase the backup. If you're not sure, just remember not to use Windows to access anything on the external drive used for Time Machine in the future.

To go back to what is on the external drive. When you look at root of the drive there are only two items, is that correct? Install Mac OS and Backups.backupdb ?

Since erasing and reinstalling on you Mac, have you added many things? Is there a lot of difference between the backup, and what is on the Mac now?

If not then you can copy just whats new onto the external, and recover from the backup fully. Once you have fully recovered from the backups and copied the individual items that are backed up since the Time Machine was stopped, the external drive can be erased and new backups started.

Customer: replied 4 years ago.



I finally just went ahead and erased my backup drive to make it available.


I only have one partition on my internal hd now, since having done the reformat and os reinstall trying to fix these problems.


I also went ahead and did a TM backup, and now my internal and backup drives are identical.


The email problems and Ical problems persist. Messages in email are continuing to ask for passwords, taking VERY long to load new emails, not being able to successfully move emails to the trash, and not being able to send emails and getting the message, "server is off-line'. Very little consistency to this problem...happens, then doesn't happen, then happens again without apparent cause.


The calendar issues are that the Ical on my computer and on my Iphone are not syncing correctly. There are calendar entries on my computer that are not showing up on my Iphone. This problem didn't exist before all of these issues began a few months ago.


Thx~ Barry

Hi Barry,

I think the Mail and Calendar databases are corrupt, which can happen if they become too large.

I recommend starting with fresh databases for Mail and iCal, but first verify that the backups are accessible.

With Mail as the active application, enter Time Machine. Can you see a timeline on the right hand side that has white marks that represent incremental backups?

If there are backups for Mail and iCal, then it's best to start fresh with the data in those applications. When you have setup Mail and iCal again, and if there are any iCal events or Mail items you want from before starting a clean slate, you can access Time Machine and pull them from the backups.

First please verify that you can access the backups with Time Machine.

Best regards,
Customer: replied 4 years ago.

Hmmm...ok. I guess I don't quite see how they could be too large, as they have only been established since I reformatted the internal drive and reinstalled my os....and then set them up. This has only been in the last 2-3 months, max.


The only backups on the external hd (via TM) will be those I made in the last 2 days, and they are only of these 'newly' set up Mail and Ical apps from the last 2-3 months, as mentioned above.


Yes, there are incremental backups in TM, but only back to Oct 1st, as that is when I erased the external and did a TM backup.


I guess I can access these items from Ical and Mail backups, but I am not sure how to do that.


I don't know what you mean exactly by 'setup Mail and Ical' you mean to delete the apps and start all over, or (in Mail) to delete all the accounts and set them all up again? In Ical, do you mean I should delete all the calendars and start again?


Again, I DO want to maintain items from the backups of Mail and Ical, but I don't know how to do that.