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Mac mail 7.3 receiving but not sending

Hello everyone,


I have been stuggling with this problem for three days now. I set up a new e-mail account (for a new job) and the new account will receive fine but not send. Here is the general set of steps that I followed:


* Used IMAP unsecured - smtp port 25. Failed due to port blocking

* Used IMAP unsecured - smtp port 587. Works on other servers but this one not.

* Used IMAP and smtp secured with SSL - smtp port 465. Failed.


The last one is what I believe I should be using. I get the standard "Could not connect to this SMTP server..." message on connection doctor, and all I get from the log is:


INITIATING CONNECTION Jun 10 11:04:13.633 host:vps2955.inmotionhosting.com -- port:465 -- socket:0x0 -- thread:0x608002468c00



CONNECTED Jun 10 11:04:14.278 [kCFStreamSocketSecurityLevelNone] -- host:vps2955.inmotionhosting.com -- port:465 -- socket:0x600000ad8d40 -- thread:0x608002468c00


With no "READ" or "WROTE" messages or anything else. The "kCFStreamSocketSecurityLevelNone" seems odd, but I've seen that elsewhere. I've also tried:


* Turning off SSL and using 465 - failed

* Deleting all related keychain items - no effect (after accepting the cert)

* Running keychain first aid - no problems


I contact inmotion hosting and they said my settings all look right. They can probe further, but I need to coordinate with my boss to get permissions for them to do that (maybe later today).


One additional thing - using network utility I am able to see port 465 on this server as expected.


I'm at a loss. I've set up many, many e-mail accounts in the past and this is the first time I have ever had these sorts of problems. Help!!!

MacBook Pro (15-inch Mid 2010), iOS 7.1.1

Posted on Jun 10, 2014 11:28 AM

Reply
13 replies

Jun 10, 2014 12:54 PM in response to CaptainAstro

If you're really sure that all the settings are correct, and if a phone can connect to the same server, with the same settings, from the same network (not a cellular network), then maybe the server is denying simultaneous connections from more than one client, or else you've managed to find one of the few mail hosts that are incompatible with OS X Mail. You might have better luck with another mail client, such as Thunderbird.

Jun 10, 2014 5:07 PM in response to dianeoforegon

The full e-mail address is there. The settings are exactly what I entered in my iPhone and in Thunderbird.


Two interesting things:


1. I downloaded and tried Thunderbird. It works fine. However....


2. It complained about an expired certificate, and when I told it to accept it anyway Thunderbird was able to send. In the keychain application I see the cert, see that it's expired, and have set it to "trust always" for everything (overkill, but I wanted to be sure). Still no luck from


This seems to indicate that there might an issue with mail with respect to the expired certificate. I can't find anything in a google search similar to this. I'll contact the service provider to see about fixing the expired cert, but it would be good if I could override mail and accept the cert anyway.


--mark

Jun 10, 2014 5:18 PM in response to CaptainAstro

Under no circumstances should you ever change the trust settings of any SSL certificate, unless you created it yourself. That's just about the most dangerous thing you can do with a computer.

Back up all data, then take each of the following steps that you haven't already taken. Stop when the problem is resolved.

Step 1

From the menu bar, select

 ▹ System Preferences... ▹ Date & Time
Select the Time Zone tab in the preference pane that opens and check that the time zone matches your location. Then select the Date & Time tab. Check that the data and time shown (including the year) are correct, and correct them if not.

Check the box marked
Set date and time automatically

if it's not already checked, and select one of the Apple time servers from the menu next to it.
Step 2

Triple-click anywhere in the line below on this page to select it:

/System/Library/Keychains/SystemCACertificates.keychain

Right-click or control-click the highlighted line and select

Services Show Info


from the contextual menu.* An Info dialog should open. The dialog should show "You can only read" in the Sharing & Permissions section.

Repeat with this line:

/System/Library/Keychains/SystemRootCertificates.keychain


If instead of the Info dialog, you get a message that either file can't be found, reinstall OS X.

*If you don't see the contextual menu item, copy the selected text to the Clipboard by pressing the key combination command-C. Open a TextEdit window and paste into it by pressing command-V. Select the line you just pasted and continue as above.

Step 3

Launch the Keychain Access application in any of the following ways:

☞ Enter the first few letters of its name into a Spotlight search. Select it in the results (it should be at the top.)

☞ In the Finder, select Go Utilities from the menu bar, or press the key combination shift-command-U. The application is in the folder that opens.

☞ Open LaunchPad. Click Utilities, then Keychain Access in the icon grid.

In the upper left corner of the window, you should see a list headed Keychains. If not, click the button in the lower left corner that looks like a triangle inside a square.


In the Keychains list, there should be items named System and System Roots. If not, select
File Add Keychain

from the menu bar and add the following items:

/Library/Keychains/System.keychain /System/Library/Keychains/SystemRootCertificates.keychain


From the Category list in the lower left corner of the window, select Certificates. Look carefully at the list of certificates in the right side of the window. If any of them has a a blue-and-white plus sign or a red "X" in the icon, double-click it. An inspection window will open. Click the disclosure triangle labeled Trust to disclose the trust settings for the certificate. From the menu at the top, select


When using this certificate: Use System Defaults


Close the inspection window. You'll be prompted for your administrator password to update the settings. Revert all the certificates with non-default trust settings. Never again change any of those settings.

Step 4

Select My Certificates from the Category list. From the list of certificates shown, delete any that are marked with a red X as expired or invalid.


Export all remaining certificates, delete them from the keychain, and reimport. For instructions, select
Help Keychain Access Help

from the menu bar and search for the term "export" in the help window. Export each certificate as an individual file; don't combine them into one big file.
Step 5

From the menu bar, select

Keychain Access Preferences... Certificates

There are three menus in the window. Change the selection in the top two to Best attempt, and in the bottom one to CRL.


Step 6

Triple-click anywhere in the line of text below on this page to select it:

/var/db/crls

Copy the selected text to the Clipboard by pressing the key combination command-C. In the Finder, select

Go Go to Folder...

from the menu bar and paste into the box that opens by pressing command-V. You won't see what you pasted because a line break is included. Press return.

A folder named "crls" should open. Move all the files in that folder to the Trash. You’ll be prompted for your administrator login password.

Step 7

Restart the computer, empty the Trash, and test.

Jun 12, 2014 11:21 AM in response to Linc Davis

Thanks Linc,


Well, it's still not working. Here's what I've done so far:


  • I contacted the email service provider and told them about the expired certificate. They confirmed that it expired, and created a new one.
  • I deleted the old cert with the keychain app and restarted mail. The new cert showed up. Still not working.
  • I followed your steps above. Still not working.
  • I deleted the new cert with the keychain app and restarted mail. Still not working.


So, I'm at a loss. For the moment I will use Thunderbird with this account. It's not ideal, but at least I can work. I'll continue to monitor this thread as I'd love to hear any other ideas about how to address this.


Thanks for all the advice so far...


--mark

Jun 12, 2014 9:03 PM in response to Linc Davis

Yea, that was my thought, but it's the service that the company is using so I don't have much say at the moment. Perhaps next year we can step up to a more professionally run service.


One last question, short of using wireshark, is there any way to look at the protocol transactions with better fidelity than connection doctor? That may tell me more about what's going on. If not, I may dig out wireshark this weekend and see what's really happening on the wire.


Anyway, thanks again for the assistance.


--mark

Apr 25, 2015 12:31 PM in response to Eric Root

After working normally with my existing mail account settings, Mail 7.3 has abruptly decided that none of my out-going mail servers are working. All of them are grayed out in the list of out-going mail servers.


If I go into each account I may or may not be able to re-designate its out-going mail server, depending on time of day, humidity, and the condition of the NASDAQ.


Mail 7.2/.3 have been fritzy some some time, causing me to think about switching to Thunderbird Mail, which seems to be the only alternative to mail.app.

Mac mail 7.3 receiving but not sending

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