Apple Mail and Exchange Server

I have Apple mail with many accounts included two Exchange accounts. As soon as my MacBook Pro with ML goes into screensaver the exchange servers disconnects and the list of emails dissapear in the inbox. I need to restart Apple mail and then they are back. I need to to restart Apple mail several times daily. Any ideas or workaround?

Others at the same issues.
Here is the thread I was referring to. Hopefully you may find some solutions inside.
https://discussions.apple.com/thread/4136482?start=0&tstart=0

Similar Messages

Apple Mail and Exchange Out of Office Not Working

Has anyone had issues with Yosemite Mail and setting Out of Office for Exchange 2010?
I can set Mail to send Out of Office replies but cannot change the scheduled dates from 2/12/1982, 10:00 AM. Even when I do set it, it does not seem to send the OOO notifications. I can set it just fine on my iPhone 6 and Mavericks Mail worked fine for setting the OOO.
I deleted my account several times and reset it and I can get all my Mail back just fine but OOO still doesn't work correctly. I wanted to try to change the server settings but Mail doesn't allow you to do that for auto connect Exchange accounts.
Because of this (and my concern with reported issues with updating meetings), I switched back to Outlook 2011 until these bugs get ironed out. This is too bad because I love the notifications feature for Apple's programs.
I'm running on a 2014 13" MacBook Pro.

Same issue here. I can see these error messages repeating when I'm trying to change the date.
2014-12-11 02:29:23,447 Mail[87049]: (
0   CoreFoundation                      0x00007fff900d564c __exceptionPreprocess + 172
1   libobjc.A.dylib                     0x00007fff990b86de objc_exception_throw + 43
2   CoreFoundation                      0x00007fff900d86bd -[NSObject(NSObject) doesNotRecognizeSelector:] + 205
3   CoreFoundation                      0x00007fff9001fa84 ___forwarding___ + 1028
4   CoreFoundation                      0x00007fff9001f5f8 _CF_forwarding_prep_0 + 120
5   AppKit                              0x00007fff8f1e61de -[NSDatePickerCell(NSInternal) _constrainAndSetDateValue:timeInterval:sendActionIfChanged:beepIfNoChange:retur nCalendarToHomeMonth:preserveFractionalSeconds:] + 259
6   AppKit                              0x00007fff8f1ea5da -[NSDatePickerCell(NSTextFieldWithStepperDatePickerInternal) _commitSubfieldFieldChanges] + 1292
7   AppKit                              0x00007fff8f1e6528 -[NSDatePickerCell(NSInternal) _finishPendingEdit] + 53
8   AppKit                              0x00007fff8f1e969d -[NSDatePickerCell(NSTextFieldWithStepperDatePickerInternal) _textFieldWithStepperTrackMouse:inRect:ofView:untilMouseUp:] + 648
9   AppKit                              0x00007fff8f1e51c8 -[NSDatePickerCell trackMouse:inRect:ofView:untilMouseUp:] + 159
10 AppKit                              0x00007fff8f018139 -[NSControl mouseDown:] + 714
11 AppKit                              0x00007fff8f511f4f -[NSWindow _reallySendEvent:] + 12827
12 AppKit                              0x00007fff8ef9c50c -[NSWindow sendEvent:] + 368
13 AppKit                              0x00007fff8ef4e096 -[NSApplication sendEvent:] + 2238
14 Mail                                0x0000000106c767d0 Mail + 272336
15 AppKit                              0x00007fff8eddae98 -[NSApplication run] + 711
16 AppKit                              0x00007fff8edc62d4 NSApplicationMain + 1832
17 libdyld.dylib                       0x00007fff8fbe05c9 start + 1
18 ???                                 0x0000000000000001 0x0 + 1
2014-12-11 02:29:23,613 Mail[87049]: -[NSDateComponents timeIntervalSinceDate:]: unrecognized selector sent to instance 0x6180005423c0
2014-12-11 02:29:23,613 Mail[87049]: -[NSDateComponents timeIntervalSinceDate:]: unrecognized selector sent to instance 0x6180005423c0

Connecting Apple Mail to Exchange Server

I just bought a new IMac and have been trying to pop to my university email account. It is on an exchange server. I have successfully popped to this account using Outlook, my IPhone and other email programs, but when I try to set up Mail (version 2.1.1), it cannot connect at the point where it says "Checking connection to POP server"....it always bombs out with a mesage that says "The POP server xxxx is not responding"
Given that I'm able to connect with other Mac products (IPhone) as well as non Mac products, this seems like some probelem specific to the OS system. Any suggestions on how to connect would be greatly appreciated.
Thanks
Allen

I'm have an exchange account at a university which works ok. When setting up the account with the mail wizard, I choose exchange from the menu instead of POP. I've also read where users have chosen IMAP.
I'm not familiar with the iphone setup so I can't comment about why iphone POP would work with exchange server.
I know I had to use the university web site and follow their setup info for exchange server. They didn't have an apple version so I just applied what they suggested the best I could.

Mail and Exchange Server Name Auto Resolution

Here's the configuration:
Exchange 2003 Server mail system (multiple servers)
Apple Mail under Leopard and Tiger (all of the updates applied)
Active Directory user accounts (Macs are NOT bound to A.D.)
When running the Apple Mail New Account configuration using the account type "Exchange", Mail does not seem to want to resolve the incoming mail server field to the proper Exchange server on which the user's mailbox is homed. This causes the setup process to fail. Entourage 04 and legacy mail clients (Outlook 2001, 98 and Exchange 5) all can resolve this with no problem. Since Mail uses WebDAV, I've tried using our OWA URL in that field as well, however that doesn't work either. I can get around this by locating where the user's mailbox is on one of our 8 Exchange boxes and then inputting the exact server name, but having to get that information every time makes things difficult for our field techs.
This is definitely not a problem with our DNS either as that resolves fine.
Anyone else seeing this or have a suggestion?

http://davmail.sourceforge.net/osximapmailsetup.html
http://davmail.sourceforge.net/faq.html
http://davmail.sourceforge.net/macosxsetup.html

Help: Apple Mail and Exchange - Internal/External servers issues

Hi, I'm new here... coming from the dummy pc world...
I am using Apple Mail in 10.7 connected to a MS Exchange 2007. I first configured the exchange account while out of the office (the firm is overseas), and had the server with the IP address and SSL at 443 port. Everything worked fine.
Then I went to the office for meetings and had to recofigured the whole enchilada (the IP address would not work as internal server while in the network). I input the internal server (a weird address "alm-srv06") and moved the IP address to the external server. It also worked fine.
But, when I came back (out of the office), the account is not working anymore. Obviously, the internal server doesn't work and the external server is not kicking in. I have even manually switched the servers, bringing the IP address to the internal server and keeping the wierd internal server address as the external server (so I can remember the config later on when I go back to the office overseas), but it is still not working...
Any thoughts?
Thanks.

Hi, I have a slightely different problem. I first configured the exchange server account while out of the office (the firm I joined is overseas), and had the server with the IP address and SSL at 443 port. Everything worked fine.
Then I went to the office overseas for meetings and had to recofigured the thing (the IP address would not work as internal server while in the network). I input the internal server (a weird address ("alm-srv06") and moved the IP address to the external server. It also worked fine.
But, when I came back, the account is not working anymore. Obviously, the internal server doesn't work and the external server server is not kicking in. I have even manually switched the servers, bringing the IP address to the internal server and keeping the internal server as external (so I can remember the config later on when I go back to the office overseas), but it is still not working...
Any thoughts?
Thanks.

Trying to go from Entourage to Apple Mail using Exchange Server

I am currently using Entourage and successfully connecting to my company's Exchange Server. I am sick of how Entourage wraps text and poorly handles HTML emails, and a host of other annoyances. However, I cannot for the life of me get Mail to work with my Exchange Server. The input fields on the account setup are not the same between Entourage and Mail. Any pointers would be much appreciated. Thanks.

Same goes for me. I know IMAP is not enabled. Entourage WORKS within my workplace network but mail.app will not. Entourage is OK using IP addresses like 10.1.1.30 where mail.app doesn't know what to do with them. Again, all this is within the workplace network. Outside the network, Entourage does not work and all I have to use in Outlook Web Access. I am fine with the inside-outside situation. I just would like a workaround to be able to use my mail.app within my workplace Exchange environment.

Mail and Exchange server

Hi,
I work at an all Windows company, being one of the only Mac there, I almost have no support and I'm stuck. I have Mail.app configured with our Exchange server, I can receive messages but I can only send them to people in our company, any address outside get stuck in the outbox with a message asking to try another server.
Anybody got an idea how to fix that ?

I had the same issue but only when I was sending outside of my company's network. The issue was traced to the internet service provider (ISP). Here is what was done to correct for it:
+ Register your email address with your ISP. Contact your ISP and they will walk you through it.
+ When you are connected through your ISP be sure to use their outgoing ISP settings, not the Exchange outgoing settings. In Mail, just below the to and cc you will see a drop down for your various email addresses and drop down for outgoing servers.
Hope this helps,
Mike

IOS 7 Mail and Exchange server - no more threaded mail messages?

In iOS 6, Exchange-hosted Mail would show entire message threads, meaning you'd see your reply as a separate message. In iOS 7, it appears that unless the party responds, you won't have an email 'conversation' and you don't know what you've said (or whether your message got through) unless you look in "Sent Mail."
Mail.app in Mountain Lion does not work this way. There, all messages are threaded.
Anyone know how to fix this?
thanks!

Hello whizzo,
Thank you for using Apple Support Communities!
Check out this setting to see if the option to group by thread is turned off or on.
Mail settings
Go to Settings > Mail, Contacts, Calendars, where you can:
Turn on Organize by Thread to group related messages together
From: iPhone User Guide
http://manuals.info.apple.com/MANUALS/1000/MA1565/en_US/iphone_user_guide.pdf
Regards,
Sterling

OSX Lion Mail and Exchange Server

My ITS person says that OSX Lion Mail "doesn't allow for exchange accounts so calendars etc don't work".
Is this true?
Thanks!

Again, both of you have been really helpful. Thank you so much.
If you are both still on this thread, I would like to ask about solutions to a space problem:
My primary computer is a MacBook Pro (Lion 10.7.3), where I am running Entourage 2008 (13.1.2). Because I have limited space on my MBP for housing old emails (under "On My Computer"), I created a server from an old Mac in my office. Then, using Entourage 2008 from my MBP, I created an additional IMAP account on the old Mac server, with subfolders for "email_2005", "sent_email_2005", "email_2006", "sent_email_2006", etc. This is where I archive all my old email. The nice thing about setting it up this way is that I can search any or all of these folders anytime, and from any location, directly from my Entourage 2008 app on my MBP, yet they take up no space on my MBP.
First of all, I suspect there were easier ways to archive off emails from my MBP, but after searching and asking for weeks, this is what I settled on and it has served me well for years.
But now, my old Mac really is getting old and I'm worried it will die at some point. Plus I'm not thrilled about trying to maintain the server software on this old Mac.
I also have space on a shared drive maintained by ITS, that's backed-up nightly. This would be an ideal place to house archived mail folders. Then I could take down the server on my old Mac and not worry about it anymore. Unfortunately, I have not been able to set up an IMAP account on my shared drive space (I suspect it's against the ITS rules of this drive).
Entourage 2008 does not permit me to designate where "On My Computer" folders are housed (they have to be on the same computer running the Entourage 2008 app). If I could designate the location of "On My Computer" folders, a simple solution would have been to just locate them on the shared drive and I wouldn't have to bother with creating additional IMAP accounts housed elsewhere.
Questions:
1) Does Outlook 2011 or Lion Mail permit designating the location of local files (off my primary MBP) for archiving emails?
2) Is there a simpler solution to archiving emails off my laptop, but that would also allow them to be conveniently searchable from within a mail app on my laptop?
Sorry for the long-winded questions.
Thank you again.

Mail and Exchange 5.5 Server (Round 2) "Rejected Passwords"

Mail and Exchange 5.5 Server (Round 2) "Rejected Passwords"
This one is huge, as you may have seen in my other replies to Mail and Exchange Server, I have had this working for over a year no issues.
Every once in a while I get a user that I setup and all of the sudden their password on the Exchange (5.5) Mail server (running IMAP, OS X Mail app)
is REJECTED.
This is just no good, and still to me a Mystery.
Has anyone seen this?
It seems there is some corruption happening on the Exchange Server, with the users accounts, preferences, settings.
The one way to fix it, (that I have seen) and the Windows server guys hate this, but I say too bad, completely move the afftected User's Exchnage e-mail account to another Exchanage NT mail server (they have 6 old NT 4, Exch Servers), once that is done, Mac OS X Mail app connects fine and ha no more issue with Rejecting passwords.
Any feedback appreciated, thanks,
[email protected]

I think I have the same problem without Exchange involved. I have seven different email accounts and two of them are acting like you describe: changes like deleting doesn't reflect on other clients (like mobile phone email client and webmail).
This also happens with read emails showing up unread so that if the email is been read and deleted same message can appear as new and when that message is deleted I can see two separate items of that same email message.
Also all marks of reply, forward or flagged are gone when the email show up as new again.
My service provider said that updates to Mail.app have previously made some big changes to way how it acts with email servers and thought that Mail is misbehaving with my two email systems.
I am using IMAP protocol with all accounts.
Thanks for any info and help!

New IMAP account won't appear on Apple Mail and yet wipes server

I have a problem with Apple Mail and a new IMAP account I've created.
I have one IMAP account (mail@*.com) which works fine and then recently I created a second IMAP account on that same server (property@*.com). I copied the details from the server to Apple Mail and yet as soon as I set up the account on Apple Mail then the test mails I send vanish from the server and do not show up in Apple Mail. When I remove that account on my Apple Mail then I can send messages to via webmail which show up on the server again.
Similarly when I use Thunderbird as my mail client then the property@*.com IMAP mail shows up fine.
Is there some conflict with having two IMAP accounts from the same server? is there any way I can get round that - set up an alias to have my property mail hived off to a different account / or even folder?
I would appreciate help... although I notice that 4 out of 5 of my last posts didn't get answered...
Alistair
<Edited by Host>

It's a bad idea to post your email addresses - it's an invitation to spam - and I've asked the Moderators to remove them.

Differences in Apple Mail and Entourage

I am running both Apple Mail and Entourage. I've noticed some differences I'd like to have someone explain to me. Both have accounts connected to Exchange.
1. Apple Mail can access the Exchange server from any internet connection. Entourage has to be on the same subnet in order to connect. Why is this happening?
2. I just rebooted my Exchange server and Entourage will send and receive but Mail will only send. What would cause that to happen?
gbs

Let me answer my question. Apple mail uses IMAP and Entourage uses OWA. That doesn't necessarily answer why Entourage can't access the server when off the subnet.
When rebooting the server the IMAP protocol was not automatically started which prevented Mail from receiving messages.

Apple Mail and GoogleMail via IMAP

Disclaimer: Apple does not necessarily endorse any suggestions, solutions, or third-party software products that may be mentioned in the topic below. Apple encourages you to first seek a solution at Apple Support. The following links are provided as is, with no guarantee of the effectiveness or reliability of the information. Apple does not guarantee that these links will be maintained or functional at any given time. Use the information below at your own discretion.
_*Apple Mail and GoogleMail via IMAP*_
As posts concerning the setup of Apple Mail for GoogleMail IMAP access become more frequent on Apple Discussions, I decided to collect some of the most asked-for info in one place. The following hints are intended to provide enough info for anyone who wants to get started with Google Mail IMAP and Mail.app.
As you might have noticed already, GoogleMail behaves differently from other IMAP accounts in some respects. One of the underlying reasons is its use of labels instead of folders (i.e. instead of moving messages to different folders – like e.g. Private and Work – in order to establish some order, rather there are labels tagged to the messages). Because of this a particular setup of Apple’s Mail client is required.
*Activating IMAP for Google Mail*
If you haven’t activated access via IMAP for Google Mail already, follow the instructions given by Google [here|http://mail.google.com/support/bin/answer.py?answer=77695&topic=13294]. It boils down to this:
1) Sign in to Gmail.
2) Click "Settings" at the top of any Gmail page,
3) click "Forwarding and POP/IMAP",
4) select "Enable IMAP".
5) Click "Save Changes".
*Creating a new account in Apple Mail*
To add a Google Mail IMAP account in Mail.app, go to File > Add Account. A wizard will open which prompts you to insert your Name, the eMail-address of the new account and the password. Don’t use the option for automatic configuration if it’s available. Info on what to type into the different fields can be obtained from Google [here|http://mail.google.com/support/bin/answer.py?answer=78799&topic=12814]. The most important are:
1) Incoming Server: imap.gmail.com, port 993 (using SSL)
2) Outgoing Server: smtp.gmail.com, port 465 or 587 (using SSL)
3) Your account name is your full email address including "@gmail.com" (without the quotation marks)
*Configuring the Google Mail account in Apple Mail*
After you have added your Google Mail IMAP account to Mail.app, you’ll find a section for Google Mail in Mail.app’s sidebar with subfolders like "All Mail" (which has in turn several subfolders) and folders for each label you created with GoogleMail. Now you have to configure the account properly. Despite what [Google recommends|http://mail.google.com/support/bin/answer.py?answer=78892&topic=1281 4], I found the following settings to work best for me.
In the sidebar, navigate to the subfolders Trash/Sent/Drafts/Junk of "Google Mail" (the one with the white folder icon instead of a blue one) in turn and go to "Mailbox" menu > "Use this mailbox for..." > Trash/Sent/Drafts/Junk respectively. Afterwards these folders show up as subfolders to the main Trash/Sent/Drafts/Junk folders in the sidebar (and at the same time disappear from the GMail section). Among others this step is necessary because of Google Mail’s implementation of labels. E.g., as Google states [here|http://mail.google.com/support/bin/answer.py?answer=78892&topic=12814]:
Messages that are deleted from an IMAP folder (...) only have that label removed and still exist in All Mail
So if you want to delete a message you have to set the option to "Use this mailbox for… Trash" as described above. Same applies to sent messages etc.
Furthermore, make sure every checkbox in Mail's Preferences > Accounts > GoogleMail > Behavior is checked . (Some will already and automatically be checked when you apply the option "Use this mailbox for..." as described above).
*Some basic troubleshooting tips*
1) If your counter for unread messages in Mail.app doesn’t refresh properly, go to "Mailbox" menu > "Sync all accounts".
2) If you have set up a Smart Mailbox in Mail e.g. for unread messages and every unread message of Google Mail shows up twice, then add the criterion "Message is not in mailbox" > "All Mail", and set the requirement for messages to comply with ALL conditions (instead of ANY). This is necessary because of every message there is a copy stored in All Mail.
I hope these info will be regarded as helpful by anyone who tries to get started with Google Mail and experiences some problems on the way.
The links given were accessible as of September, 3rd, 2008. The setup was tested on a MacBook with OS X 10.5.4 Leopard and Mail 3.4 (928/928.1).
Good computing.
floba
(Note: the above given hints are personal suggestions and I don’t assume liability for any disorders that might occur after applying the described steps.)
Do you want to provide feedback on this User Contributed Tip or contribute your own? If you have achieved Level 2 status, visit the User Tips Library Contributions forum for more information.

Disclaimer: Apple does not necessarily endorse any suggestions, solutions, or third-party software products that may be mentioned in the topic below. Apple encourages you to first seek a solution at Apple Support. The following links are provided as is, with no guarantee of the effectiveness or reliability of the information. Apple does not guarantee that these links will be maintained or functional at any given time. Use the information below at your own discretion.
_*Apple Mail and GoogleMail via IMAP*_
As posts concerning the setup of Apple Mail for GoogleMail IMAP access become more frequent on Apple Discussions, I decided to collect some of the most asked-for info in one place. The following hints are intended to provide enough info for anyone who wants to get started with Google Mail IMAP and Mail.app.
As you might have noticed already, GoogleMail behaves differently from other IMAP accounts in some respects. One of the underlying reasons is its use of labels instead of folders (i.e. instead of moving messages to different folders – like e.g. Private and Work – in order to establish some order, rather there are labels tagged to the messages). Because of this a particular setup of Apple’s Mail client is required.
*Activating IMAP for Google Mail*
If you haven’t activated access via IMAP for Google Mail already, follow the instructions given by Google [here|http://mail.google.com/support/bin/answer.py?answer=77695&topic=13294]. It boils down to this:
1) Sign in to Gmail.
2) Click "Settings" at the top of any Gmail page,
3) click "Forwarding and POP/IMAP",
4) select "Enable IMAP".
5) Click "Save Changes".
*Creating a new account in Apple Mail*
To add a Google Mail IMAP account in Mail.app, go to File > Add Account. A wizard will open which prompts you to insert your Name, the eMail-address of the new account and the password. Don’t use the option for automatic configuration if it’s available. Info on what to type into the different fields can be obtained from Google [here|http://mail.google.com/support/bin/answer.py?answer=78799&topic=12814]. The most important are:
1) Incoming Server: imap.gmail.com, port 993 (using SSL)
2) Outgoing Server: smtp.gmail.com, port 465 or 587 (using SSL)
3) Your account name is your full email address including "@gmail.com" (without the quotation marks)
*Configuring the Google Mail account in Apple Mail*
After you have added your Google Mail IMAP account to Mail.app, you’ll find a section for Google Mail in Mail.app’s sidebar with subfolders like "All Mail" (which has in turn several subfolders) and folders for each label you created with GoogleMail. Now you have to configure the account properly. Despite what [Google recommends|http://mail.google.com/support/bin/answer.py?answer=78892&topic=1281 4], I found the following settings to work best for me.
In the sidebar, navigate to the subfolders Trash/Sent/Drafts/Junk of "Google Mail" (the one with the white folder icon instead of a blue one) in turn and go to "Mailbox" menu > "Use this mailbox for..." > Trash/Sent/Drafts/Junk respectively. Afterwards these folders show up as subfolders to the main Trash/Sent/Drafts/Junk folders in the sidebar (and at the same time disappear from the GMail section). Among others this step is necessary because of Google Mail’s implementation of labels. E.g., as Google states [here|http://mail.google.com/support/bin/answer.py?answer=78892&topic=12814]:
Messages that are deleted from an IMAP folder (...) only have that label removed and still exist in All Mail
So if you want to delete a message you have to set the option to "Use this mailbox for… Trash" as described above. Same applies to sent messages etc.
Furthermore, make sure every checkbox in Mail's Preferences > Accounts > GoogleMail > Behavior is checked . (Some will already and automatically be checked when you apply the option "Use this mailbox for..." as described above).
*Some basic troubleshooting tips*
1) If your counter for unread messages in Mail.app doesn’t refresh properly, go to "Mailbox" menu > "Sync all accounts".
2) If you have set up a Smart Mailbox in Mail e.g. for unread messages and every unread message of Google Mail shows up twice, then add the criterion "Message is not in mailbox" > "All Mail", and set the requirement for messages to comply with ALL conditions (instead of ANY). This is necessary because of every message there is a copy stored in All Mail.
I hope these info will be regarded as helpful by anyone who tries to get started with Google Mail and experiences some problems on the way.
The links given were accessible as of September, 3rd, 2008. The setup was tested on a MacBook with OS X 10.5.4 Leopard and Mail 3.4 (928/928.1).
Good computing.
floba
(Note: the above given hints are personal suggestions and I don’t assume liability for any disorders that might occur after applying the described steps.)
Do you want to provide feedback on this User Contributed Tip or contribute your own? If you have achieved Level 2 status, visit the User Tips Library Contributions forum for more information.

Apple Mail and Gmail IMAP

With the iPhone coming to Verizon soon, I'd like to move back to Apple Mail from Gmail, but still want to keep Gmail as my source because my domain is setup with Google Apps but mostly because of the unparalleled spam filtering Gmail has. My problem is that even though I've configured Apple Mail exactly as Google recommends (shown below), I still have some issues.
From the Mail menu, click Preferences > *Accounts > Mailbox Behaviors*
Drafts:
Store draft messages on the server > *do NOT check*
Sent:
Store sent messages on the server > *do NOT check*
Junk:
Store junk messages on the server > checked
Delete junk messages when > Never
Trash:
Move deleted messages to the Trash mailbox > *do NOT check*
Store deleted messages on the server > *do NOT check*
I want to have true IMAP functionality here, but I'm not getting it. Sent messages work fine...if I send a message, it shows up in Apple Mail in the Sent folder and when I go to Gmail it is also in the Sent folder. BUT...when I delete a message in Apple Mail it goes to the Gmail *All Mail* folder (in Apple Mail and Gmail) and never shows up in the Gmail Trash on either Apple Mail or Gmail...where it should. I've tried changing the settings under *Apple Mail > Trash* but that doesn't fix the problem.
I realize some of you might be inclined to say "It's Google problem...ask there" but I'm hoping a Gmail user here might have had this same issue before. Even as a dedicated Apple person for many years, I still can't give up Gmail and their spam filtering that Apple Mail can't come close to. Thanks for any suggestions.

Thanks, Andy. I should have posted a closure statement on this thread as I finally figured everything out. The most frustrating thing is Google's own advice at http://mail.google.com/support/bin/answer.py?answer=78892# couldn't further from correct. After many hours of experimenting with settings, I finally came up with the correct ones. In fact, I'm in the process of writing an article about it since there is simply no definitive guidance on the web that I've been able to find in the time I've searched.
Your comments are on target...everything on the *Behaviors Tab* needs to be checked (excepts Notes) and the *Delete when* settings must be set to Never. But there are a few other things that must be done, including some changes on Gmail Settings before Mail and Gmail will be perfectly synchronous. I'll post the entire solution on this forum when I finish the graphics.

Apple Mail and Sent Messages

I have been having some issues with my iCloud email account and Mavericks. I wasn't sure if this was an iCloud issue or an issue with Apple Mail. It has to do with saving Sent messages. A couple of months ago, I had some issues with Mail. I deleted the com.apple.mail and com.apple.MailServiceAgent folders in ~Library/Containers and I deleted any plist files in Preferences. It worked for a couple months. Then, about two weeks ago, I noticed Sent emails were not be saved any where on my iMac.
So, I repeated the procedure and created Mail anew. It worked great for about a week. I always have the "save sent messages to server" option turned on. Then, one day I got some kind of message that a folder called "Sent" could not be created on the server. Looking at Mail, my Sent folder was completely gone. All of my previously saved messages in Sent were moved to the folder INBOXToDos.mbox/Sent Messages.
At first I thought iCloud itself was messed up. I logged into iCloud. There was no Sent mailbox, and there was no INBOXToDo mailbox. So, now I have no sent messages anywhere in iCloud. I sent an email from Safari in iCloud, and then, iCloud created the Sent mailbox.
Still, my Mavericks iMac will not save sent messages anywhere. I need help sorting this out and don't want to lose my previous sent messages even though they seem to be stored in some wonky folder.

Where is the Sent Messages folder listed? If it is not under MAILBOXES but in an IMAP folder, select it and go to Mailbox menu, Use this mailbox for>Sent.
It should disappear and sent messages then appear in the Sent folder.

Apple Mail and Exchange Server

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