Apple Mail not sending Gmail Imap

Hey I have Gmail on my Apple Mail using Imap and it was working fine until about a week ago when it stopped sending so I tried re-adding an Imap account but cant even create one
Anyone else had this problem, any ideas?

Hello,
What size are these attachments & what extention/file type are they?
gMail has been known to refuse say .zip files, & of course attachments over a certain size.
One big drawback on Apple Mail is that if you have a malformed or non compliant eMail, it'll prevent anything beyond that, just keeps trying & failing to progress to the next one.
Not certain, but this can fix myriad Mail problems...
Safe Boot from the HD, (holding Shift key down at bootup),  it will try to repair your Disk Directory while the spinning radian is happening, so let it go, run Disk Utility in Applications>Utilities, then highlight your drive, click on Repair Permissions, then move this folder & file to the Desktop.
Move this Folder to the Desktop...
/Users/YourUserName/Library/Caches/Mail/
Move this file to the Desktop...
/Users/YourUserName/Library/Mail/Envelope Index
Reboot.
If that doesn't do it and you can afford to redo all your Rules, try these & reboot...
/Users/YourUserName/Library/Mail/MessageRules.plist
/Users/YourUserName/Library/Mail/MessageRules.plist.backup
Note, in 10.5 & up /Users/YourUserName/Library/Caches/Mail/ may or may not exist.

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    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.
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    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.
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    (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.
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    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.
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    3) click "Forwarding and POP/IMAP",
    4) select "Enable IMAP".
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    *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)
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    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.

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