Mail Trouble

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So I recently upgraded OS to 10.5.6 and I can receive email. The problem is that when I try to send an email, it shows a symbol in motion next to the send airplane icon but never sends it. I believe settings in mail are correct. Any suggestions?
 
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Does anyone have a clue? There are items in the outbox but it doesn't seem to be sending them.

I can receive email fine but can't send it. I tried copying the settings I use from my laptop (Windows XP) with Outlook Express to mail on my Mac but have no luck. Anyone out there have an OptOnline email account that can provide the settings they use??

Thanks
 
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Have you referred to this at Optimum? And make sure that Mail.app hasn't set use SSL.
 
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Thank you for the Opt email link. What do you mean by "make sure that Mail.app hasn't set use SSL." Sorry - new to this
 
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Your Mac's Specs
Late 2013 rMBP, i7, 750m gpu, OSX versions 10.9.3, 10.10
If you launch mail
go to the mail drop-down, select preferences
under accounts, you will see Outgoing Mail Server (SMTP), click the little arrows that point up and down, select "Edit Server List"
With your email server highlighted (which it will be if there is only one entry) there should be a button about mid window that says Advanced, click it
There is a check box there: Use Secure Sockets Layer (SSL) make sure it's unchecked.
 
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Ok I unchecked that box. It is now saying my outgoing mail server is offline and the box for use only this server is checked. Still can't get any mail
 
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I had the same problem, this fixed it.
Remove the com.apple.Mail.plist located in the ~/Library/Preferences/ folder. You will have to set up mail again but that might fix it.
 
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I had the same problem, this fixed it.
Remove the com.apple.Mail.plist located in the ~/Library/Preferences/ folder. You will have to set up mail again but that might fix it.

Hey jram i got the same trouble as PhillyEagles5 did, except i cant find the com.apple.Mail.plist file in that folder. The SSL Checkbox is not selected, and also for me, outgoing mail server says offline. Ive Just got my first mac about 3 weeks ago, so far im really loving it, just get a little lost at times haha.
 
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Are you looking in the correct folder - there is a Library Folder at root level but you want the one that is in the Users Home folder - the one with the little house icon.
 
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OK i did find that file in the folder (was looking in the wrong place), but yeah still same problem hey. When i deleted the com.apple.Mail.plist file i had to re enter my email info, but not working hey. The file does re-appear
 

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