Emails with attachments not showing up in Sent box

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This just started last week: when I send an email with an attachment, it no longer shows up in my sent box, or my drafts box, which had always automatically happened. I went through the Disk Utilities drill, but it said everything was ok in both Permissions and Disk checks. Does anyone have any ideas of what to do? fyi: I have a fully loaded 2013 iMac with 10.9.5 OS X (Mavericks). I've been avoiding upgrading to Yosemite....would that help this situation if I did?
 
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Some questions for you:

1) What email provider are you using? (Outlook.com, Gmail, Yahoo, etc.)
2) Are you using Apple Mail.app, Web browser or another email client?
3) How big of an attachment are you sending?

If you can answer those, that would help anyone here greatly.
 
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1) Mac Mail with Charter ISP.

2) The Apple Mail App that came with my iMac (OS 10.9.5)

3) 5 MB.

Again, this never happened before with attachments up to 10 MB in size.
Hope this helps in getting this solved.....thanks!
 
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Ok cool. Thanks for the info. I'm not familiar with Charter ISP. Is it an IMAP email or POP?
 
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Charter is an IMAP.
I have a secondary Google Gmail account, which is also an IMAP,
but all of my initial emails are sent out via my main Charter email account.
Thanks.
 
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btw: I just did a quick test sending a Charter email to myself with a 2.4 MB attachment. The email arrived here fine, but again with nothing in my "sent" or "drafts" boxes which always showed up there before. Very strange. If I didn't work out of my home office, I wouldn't be making such a big deal out of it, but I can't afford to "fly blind" with business emails (as there might not always be someone on the other end to confirm "timely" email arrivals), so I really do appreciate your help.

I'm hesitant to upgrade to Yosemite, but will do so if you think that will solve the problem.
Thanks:).
 
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chscag

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Charter is an IMAP.
I have a secondary Google Gmail account, which is also an IMAP,
but all of my initial emails are sent out via my main Charter email account.
Thanks.

What happens when you send an email with an attachment using your gmail account? I realize Charter is your ISP and likely providing your high speed internet. And since you work from home, you probably have a Charter business account. (I have to tell you that I'm not a lover of Charter after having a very difficult relationship with them some years ago.)
 
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I would doubt very much if "upgrading" to Yosemite would help, and in fact may make your email problem worse.

Have you double-checked your Mail accounts for the "Mailbox Behaviours" tab?

What are the options set for deleting "Sent" messages? And I'd suggest "Never" would be appropriate. ;)
 
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What happens when you send an email with an attachment using your gmail account? I realize Charter is your ISP and likely providing your high speed internet. And since you work from home, you probably have a Charter business account. (I have to tell you that I'm not a lover of Charter after having a very difficult relationship with them some years ago.)

Just tried that, and it is in both my Sent and Drafts just as it was before. Problem
solved for now, so thank you very much for your suggestion (I should have thought of that myself:p).
Sorry to hear about your problem with Charter. I have no choice to use them as
they're still the only game in town here.
 
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I would doubt very much if "upgrading" to Yosemite would help, and in fact may make your email problem worse.

Have you double-checked your Mail accounts for the "Mailbox Behaviours" tab?

What are the options set for deleting "Sent" messages? And I'd suggest "Never" would be appropriate. ;)

That's why I had said I was hesitant to do so & probably won't. Was "upgrading" the wrong term to use, or are you saying you don't like Yosemite? No wrong answer to that, as I've heard both many pros & cons re: Yosemite.....just curious:).

Yes to your second question. The Drafts and Sent Mailbox Behaviors were already checked to store messages, and all deletes options are already set to "Never", so I'm good there. My emails with attachments sent from my Gmail account are being saved in both Sent and Drafts boxes (see my 5:19 post) so I'll just use it till I can get the Charter email account fixed.
Thanks for your's & everyone else's help.
 
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I just used "upgrading" (in quotes) to Yosemite as they say it is an upgrade from a previous version, I and some others would question their use of words. ;D

AFAIC, SL and maybe ML were better and more stable OS X versions and worked properly.

I still have to go back to SL 10.6.8 for certain things like using AppleWorks for a project that neither Pages '09 or Pages 5.x can do. Come on Apple, give us a REAL upgrade!! :Angry-Tongue:
 
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I just used "upgrading" (in quotes) to Yosemite as they say it is an upgrade from a previous version, I and some others would question their use of words. ;D

AFAIC, SL and maybe ML were better and more stable OS X versions and worked properly.

I still have to go back to SL 10.6.8 for certain things like using AppleWorks for a project that neither Pages '09 or Pages 5.x can do. Come on Apple, give us a REAL upgrade!! :Angry-Tongue:

I agree and hear you loud and clear on that. In my case, I can't afford to lose any functions, filters, etc. from my graphics and/or 3D software either....so for now I'll have to give "Y" a pass.
 
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My Outlook.com email account did this exact same thing about a week ago. I just deleted the account from my Mac Mail.app and then set up Outlook.com thru it again. That seemed to fix the problem for me.

Also, sorry or a VERY late reply. My life has been crazy for the past 3 weeks or so...
 

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