After update to OSX 10.9, Mail won't send attachments

Since upgrading to Mavericks (OSX 10.9), Mail (7.0) won't send email attachments using my employer's MS Exchange account. All other messages (without attachments) send just fine, and no Exchange server or account settings were changed. Attachments send just fine via the exchange web application, so it's not an account or mailbox size issue. The problem happens even with small attachments (I just tried one that was 173 kb).
After I hit send, the activity window says "adding message" for a time, then an error comes up "Cannot send message using the Exhange server" then give me an option to use my gmail or icloud which work fine.
Any ideas?

I actually was able to solve the issue using some info gleaned from other posts. I think it had to do with some exchange account settings from a prior version of Mail that were still on my machine and interfering with the new Mail app. Here's what I did to fix the issue.
Make sure I had a good backup in Time Machine (including system settings) in case something goes wrong
Delete Exchange account using "system preferences > internet accounts"
Close Mail
Show hidden files
Terminal command: defaults write com.apple.finder AppleShowAllFiles TRUE
Terminal command: killall Finder
Using Finder, locate and delete the file: ~/Library/Preferences/com.apple.mail.plist
Using Finder, locate and delete the folder(s) and all their contents: ~/Library/Mail/V2/EWS-(your exchange acct info)I actually had a couple of these "EWS" folders in there from prior times that I had setup my exchange account. Not sure why ... I just deleted them all.
Empty the recycle bin
Reboot the computer
Hide hidden files (not necessary, it's just my preference)
Terminal command: defaults write com.apple.finder AppleShowAllFiles FALSE
Terminal command: killall Finder
Open "system preferences > internet accounts" and setup Exchange account as if it were the first time.
It took a while for all my mailboxes to rebuild and everything to come in, but after the initial sync, Mail 7.0 now works perfectly with my Exchange account including sending mail with file attachments. It's actually a lot quicker to receive and send than the prior version of Mail.
It doesn't seem like a widespread problem, but I hope this at least helps you (eprasek) with your issue. Best of luck!

Similar Messages

.Mail won't send attachments

Since upgrading to OS X 10.7, Mail usually won't send attachments. It does not matter if the attachment is small (~300kb) or larger (~3MB). Mail will try to send it (and if you watch the progress bar in the lower right corner of Mail, you can see that it starts uploading the message), but then it stops. Then I get the message: "Cannot send message using the server..." Occsaionally, attachments will work, but I haven't been able to determine why. This is the case for both my desktop (10.7.2) and my laptop (10.7.3).
The e-mail affected is a g-mail account configured through IMAP. I have verified that I have internet connectivity while experiencing this problem and I can even send other e-mails w/o file attachments. I opened the Connection Doctor and everything logs in/out correctly. The details from Connection Doctor are below.
Any ideas?
Thanks.
WROTE Feb 08 08:18:55.309 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba68d5220 -- thread:0x7f9ba68ce300
CONNECTED Feb 08 08:18:59.021 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
CONNECTED Feb 08 08:18:59.022 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
READ Feb 08 08:18:59.066 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
220 mx.google.com ESMTP li19sm4211728pbb.17
READ Feb 08 08:18:59.066 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
220 mx.google.com ESMTP a5sm2518813pbh.15
WROTE Feb 08 08:18:59.085 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
EHLO [192.168.0.74]
WROTE Feb 08 08:18:59.101 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
EHLO [192.168.0.74]
READ Feb 08 08:18:59.132 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
250-mx.google.com at your service, [64.126.140.239]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
WROTE Feb 08 08:18:59.144 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
STARTTLS
READ Feb 08 08:18:59.146 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
250-mx.google.com at your service, [64.126.140.239]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
CONNECTED Feb 08 08:18:59.151 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba6b5ffc0
CONNECTED Feb 08 08:18:59.154 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba6b45550
WROTE Feb 08 08:18:59.171 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
STARTTLS
READ Feb 08 08:18:59.190 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
220 2.0.0 Ready to start TLS
READ Feb 08 08:18:59.217 [kCFStreamSocketSecurityLevelNone] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
220 2.0.0 Ready to start TLS
WROTE Feb 08 08:18:59.462 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
EHLO [192.168.0.74]
READ Feb 08 08:18:59.508 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
250-mx.google.com at your service, [64.126.140.239]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250 ENHANCEDSTATUSCODES
READ Feb 08 08:18:59.514 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba6b5ffc0
* OK Gimap ready for requests from 64.126.140.239 au13if1327927vdc.13
WROTE Feb 08 08:18:59.528 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
AUTH PLAIN (*** 52 bytes hidden ***)
WROTE Feb 08 08:18:59.541 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba3d925a0
1.29 CAPABILITY
READ Feb 08 08:18:59.547 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba6b45550
* OK Gimap ready for requests from 64.126.140.239 aj13if1332717vdc.2
WROTE Feb 08 08:18:59.586 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba67202d0
1.30 CAPABILITY
READ Feb 08 08:18:59.686 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba3d925a0
* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH
1.29 OK Thats all she wrote! au13if1327927vdc.13
READ Feb 08 08:18:59.692 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba67202d0
* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH
1.30 OK Thats all she wrote! aj13if1332717vdc.2
WROTE Feb 08 08:18:59.701 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba3d925a0
2.29 LOGIN (e-mail address edited out) **********
WROTE Feb 08 08:18:59.715 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba6d41cd0
2.30 LOGIN (e-mail address edited out) ********
WROTE Feb 08 08:18:59.816 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
EHLO [192.168.0.74]
READ Feb 08 08:18:59.866 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
250-mx.google.com at your service, [64.126.140.239]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250 ENHANCEDSTATUSCODES
WROTE Feb 08 08:18:59.885 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
AUTH PLAIN (*** 48 bytes hidden ***)
READ Feb 08 08:18:59.998 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
235 2.7.0 Accepted
WROTE Feb 08 08:19:00.016 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6d4edc0 -- thread:0x7f9ba6514970
QUIT
READ Feb 08 08:19:00.067 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba6d41cd0
* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
2.30 OK (e-mail address edited out) (name edited out) authenticated (Success)
WROTE Feb 08 08:19:00.081 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba7419930
3.30 CAPABILITY
READ Feb 08 08:19:00.139 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba3d925a0
* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
2.29 OK (e-mail address edited out) (name edited out) authenticated (Success)
WROTE Feb 08 08:19:00.159 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba6867290
3.29 CAPABILITY
READ Feb 08 08:19:00.197 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba7419930
* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
3.30 OK Success
WROTE Feb 08 08:19:00.218 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba3d925a0
4.30 ID ("name" "Mac OS X Mail" "version" "5.1 (1251.1)" "os" "Mac OS X" "os-version" "10.7.2 (11C74)" "vendor" "Apple Inc.")
READ Feb 08 08:19:00.340 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba3d925a0
* ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "64.126.140.239")
4.30 OK Success
WROTE Feb 08 08:19:00.360 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba3d925a0
5.30 LIST "" ""
READ Feb 08 08:19:00.363 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba6867290
* CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
3.29 OK Success
WROTE Feb 08 08:19:00.387 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
4.29 ID ("name" "Mac OS X Mail" "version" "5.1 (1251.1)" "os" "Mac OS X" "os-version" "10.7.2 (11C74)" "vendor" "Apple Inc.")
READ Feb 08 08:19:00.474 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba3d925a0
* LIST (\Noselect) "/" "/"
5.30 OK Success
WROTE Feb 08 08:19:00.496 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba6814e40 -- thread:0x7f9ba67202d0
6.30 LOGOUT
READ Feb 08 08:19:00.606 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
235 2.7.0 Accepted
READ Feb 08 08:19:00.623 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
* ID ("name" "GImap" "vendor" "Google, Inc." "support-url" "http://support.google.com/mail" "remote-host" "64.126.140.239")
4.29 OK Success
WROTE Feb 08 08:19:00.626 [kCFStreamSocketSecurityLevelTLSv1SSLv3] -- host:smtp.gmail.com -- port:25 -- socket:0x7f9ba6720aa0 -- thread:0x7f9ba68ce300
QUIT
WROTE Feb 08 08:19:00.643 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
5.29 LIST "" ""
READ Feb 08 08:19:00.847 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
* LIST (\Noselect) "/" "/"
5.29 OK Success
WROTE Feb 08 08:19:00.869 [kCFStreamSocketSecurityLevelNegotiatedSSL] -- host:imap.gmail.com -- port:993 -- socket:0x7f9ba62c7ae0 -- thread:0x7f9ba7419930
6.29 LOGOUT

I am going to try removing the account from mail and then setting it up again to see if it solves the issue.

Mac won't boot after updating to OSX 10.6.4

I am on my 3rd Mac that won't boot after updating to OSX 10.6.4. One MacBook Pro and two iMacs. I fixed one but the last two are getting the better of me. HD is not fried. Have tried every keyboard shortcut on startup, Disk Warrior via. Target Disk, repairing permissions in single user mode. The machines will not boot off of a CD or DVD and it will not boot up in safe mode. Something in the startup files is preventing startup. I am suspecting Sophos antivirus. I tried to uninstall it and trash it but I think it's still blocking something. Any help would be appreciated.

Got it! Not sure if removing Sophos had anything to do with it but here's what I did.
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TS3103 I have aol and cannot acesss my email after updating to osx 10.6. the help says that I need mail 4.6. I have 4.5. How do I get the correct version?

Ihave aol and cannot acesss my email after updating to osx 10.6. the help says that I need mail 4.6. I have 4.5. How do I get the correct version?

Run all software updates.
http://support.apple.com/kb/TS4424

Illustrator (CS 5.1) crashes after update to OSX Mavericks (10.9)

Illustrator 5.1 crashes while starting the app after update to OSX Mavericks (10.9)
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If you don't already have a current backup, back up all data, then reinstall the OS.* You don't need to erase the startup volume, and you won't need the backup unless something goes wrong. If the system was upgraded from an older version of OS X, you may need the Apple ID and password you used.
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I updated the maverick and now mail won't open at all

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Have you tired opening it from the Applications folder?
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After updating to IOS 8, my phone won't recognize my TV.

After updating to IOS 8, my phone won't recognize my TV via AV cable.

Same problem here on four devices, two of which aren't even running iOS 7. App updates just disappear from the app store app and the app tells me all my apps are up to date when they aren't.
This problem fixed itself on the iPhone 4 this morning after I synced it with iTunes last night. My iPad 3 is now listing app updates, but it stalls when I try to download them, so I'm updating via iTunes now.
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My problem is after updating to Yosemite does my mail client any longer. I can not even open the mail, and when I "forced closes" mail and try to open it again to go in the entered settings running the colored wheels around and allows me only to forc

My problem is after updating to Yosemite does my mail client any longer. I can not even open the mail, and when I "forced closes" mail and try to open it again to go in the entered settings running the colored wheels around and allows me only to forcing close again? does anyone have a solution to the above problem?

You mean the default OS X mail app? Try reinstalling OS X Yosemite if that's the case.
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Photoshop CS5 - colour settings in Print menu not working after update Mac OSX maverick

After upgrading to Maverick OSX on the iMac printing from CS5 via Epson R3880 is not working correctly. In Print Settings menu the drop downs for Colour and Colour Settings are greyed out. I already re-installed PS and installed the new drivers from epson. Any ideas?

but after choosing PS manages color, the options in the print menu for choosing color (color or b&W) and color settings are not available anymore. They used to be the last three years I printed with photoshop/epson 3880.
Instead they are greyed out now.
attached screenshot:
Op 30 mei 2014, om 01:47 heeft Chris Cox <[email protected]> het volgende geschreven:
Photoshop CS5 - colour settings in Print menu not working after update Mac OSX maverick
created by Chris Cox in Photoshop General Discussion - View the full discussion
If Photoshop managed color, then the controls in the printer driver are supposed to be grayed out - that's how Apple specifies drivers to work (because only one party should be managing the print color).
So what you're describing is perfectly normal.
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Display is wrong on the shadow side after updating to OSX 10.9.2

After updating to OSX 10.9.2, Aperture 3.5.1 begins to display wierd shadows. Even if the value of the black point is set to 0, the black appear to be blotching although there is no clipping appearing in the histogram. Lightroom and other 3rd party programs appear normal.

I shoot raw and I use a Canon 5D Mark II. Here is a grab from one of the pics. Note the muddy color of the green in the shadow and the black and the surrounding. This is not so when opened in lightroom or any other raw processing software.

After updating to osx 10.8.2 and itunes 10.7, iTunes crashes consistently after playing one song

After updating to osx 10.8.2 and itunes 10.7, iTunes crashes consistently after playing one song. Song progress indicator actually stops working after 30 seconds or so and iTunes can no longer be closed. However, the song finishes playing, but the next one will not start.
I tried on different computers, with different iTunes libraries, both on internal and external media. It ALWAYS happens.
Any suggestions?

I downgrade to itunes 10.6.3 and the error still appears.
I have to download this utility http://www.macroplant.com/iexplorer/download-ie3-mac.php
And I deleted this file:
/private/var/mobile/Media/iTunes_Control/iTunes/iTunesCDB
That fix the problem.
Now my iphone is working without issues on latest version of itunes 10.7

HT1338 mail icon not in dock mail won't send a pop down dox appears and when message placed a black dot appes=ars on red dot appears and then the message will go into draft ?

mail icon not in dock- mail won't send - a drop down small box appears and when a message is typed in to sent the send icon goes grey and a black dot appears on the red dot in top left side of box and the message will be sent to drafts only

Hello Bill,
Who is your eMail provider, the part after the @ sign?
In Mail's Window Menu, choose Connection Doctor, any red dots for status, if so what is the message?
Then click the Show Details button & Check again.
Mail: Can't send messages, "Cannot send message using the server smtp.xxxxx.com" alert appears...
old: http://support.apple.com/kb/TS1482

Apple Mail won't send invitations when initially closed

I just started using iCal to send invitations for appointments through Apple Mail. When Apple Mail is opened already when I create the appointment and click Send in iCal, it works fine. The mail is sent and delivered to the appropriate address.
But if Apple Mail is closed initially, the application starts and the invitation is queued up in the Outbox but is never sent. I can manually open up each invitation in Mail and send them individually, but why is the behavior different? Whether Mail is opened or closed when I send an invitation, it ought to deliver the invitation automatically. By not being sent, I may not realize the invitation hasn't been delivered, making the process very error-prone. Is there a way to guarantee the invitation actually gets sent without having to check the Outbox every time?
Is this an iCal bug or an Apple Mail bug? I saw no settings in Apple Mail for sending messages at shutdown or any other setting like this. Instead, these invitations may end up being buried in my Outbox for a very long time before I notice and by then, it may be too late.

ronright wrote:
Since I bought a new modem/router (Netgear n600), my Apple mail won't send e-mails. It will receive. My ISP is AT&T & the email accounts are via yahoo. I have a Macbook Pro with a recent OSX.
The most recent OS is currently OS 10.8.3. Your system profile confirms you are still using Mac OS X (10.7.5). If this is incorrect, please correct your profile so that you will get the correct troubleshooting suggestions/solutions.
Also, post in the OS/Mail forum of whichever OS is currently installed on your MBP. It's where the OS/Mail expert helpers hang out at.

Mail won't send without Connection Doctor having to be launched.

Mail won't send without Connection Doctor having to be launched. After running Connection Doctor, it will send, so settings all must be ok. But 15 minutes later, I need to "check again" to send mail. I read previous posts on this from a few years ago, but my laptop is running Lion.

Try just watching the "Activity" window to learn what is happening to your mail - I have found it to be most enlightening.

After update to OSX 10.9, Mail won't send attachments

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