Level 1

6 points

Mail deception - says messages are sent out but are not delivered

The Mail program appears to send my outgoing e-mail messages but does not actually do so. When I send a new message or reply to a message, Mail behaves as though the message has been sent: the spinner runs and the swoosh sound occurs when the message leaves my Outbox. The message then appears in my Sent folder. However, the mail is never received by the intended recipients. I apparently operated like this for weeks until my sister mentioned my lack of response to her e-mail a couple of weeks prior. (Honest, I really did reply.) Upon investigation I learned that others had not received messages I had sent. I then tried sending a message to myself at the same account and at my work account (different ISP) and the messages were not received.

I am using a POP account at core.com. If I access my account via the core.com webmail site, I am able to actually send messages. Getting them from the Mail program on my computer is the problem.

I noticed several other questions posted about Mail not sending messages but those queries mentioned receiving an error message or the program timed out trying to send and knowing immediately the mail was not sent. My situation seems unique in that the program is behaving deceptively - it tells me a message is sent but it is not.

I followed the steps Apple posted regarding Leopard Mail not sending messages but no success. I am using OS X5.6 on an Intel MacBook.

I have spoken with the core.com technical support staff and they assure me the problems is with the Mail program or my iMac. They are most likely correct. As an experiment I set up MS Entourage as an e-mail client for my core.com account. Entourage had no trouble sending messages to intended recipients.

I have double and triple checked the settings in Mail Preferences. The core.com technical support representative confirmed I am using the correct settings and suggested I use a different e-mail client program and forget about Apple Mail. However, I understand it is not possible to export information from Mail to a different e-mail client program so I am reluctant to make the change. The representative also suggested I remove Mail and reinstall it as a way of possibly correcting the problem. I do not want to go that route if I can avoid doing so. If that is the best approach, how do I go about saving my messages and addresses in Mail before removing Mail? Other suggestions to get Mail to behave properly?

Thank you!

iMac Intel Core Duo 2.4GHz, Mac OS X (10.5.6), MacBook Intel Core Duo 2.2GHZ

Posted on May 12, 2009 7:43 PM

46 replies

spdsail Author

Level 1

6 points

Jun 1, 2009 8:43 PM in response to Ernie Stamper

Well, I did as you suggested. The Mail program behaved in a fashion similar to before I removed the Outbox.mbox folder. The only difference being the message I sent did not go to the Outbox before being "sent out". It very quickly appeared in my Sent folder but now ten minutes later I have not received a copy at my work e-mail address or either of my voyager.net addresses with Corecomm. I plan to reinstall the Outbox.mbox folder unless you have a reason not to do so.

I ran across an Apple "E-mail Quick Assist" troubleshooting guide that suggested testing server connections using Network Utilities. Per those instructions I used Network Utilities to ping the Corecomm outgoing server using "pop.voyager.net" to check my ability to receive. That generated the following message:

"Ping has started ...

PING mail.voyager.net (207.251.194.46): 56 data bytes

--- mail.voyager.net ping statistics ---
10 packets transmitted, 0 packets received, 100% packet loss"

I don't know if "0 packets received" means the ping reached the server and was not returned to me via my incoming mail (pop.voyager.net) or if the pings were not received by the Corecomm server. I have not been having a problem receiving messages.

I also pinged "smtp.voyager.net" to test ability to send mail. That generated the following message:

"Ping has started ...

PING smtp.localnet.com (207.251.194.25): 56 data bytes
64 bytes from 207.251.194.25: icmp_seq=0 ttl=108 time=375.391 ms
64 bytes from 207.251.194.25: icmp_seq=1 ttl=108 time=346.186 ms
64 bytes from 207.251.194.25: icmp_seq=2 ttl=108 time=322.686 ms
64 bytes from 207.251.194.25: icmp_seq=3 ttl=108 time=295.292 ms
64 bytes from 207.251.194.25: icmp_seq=4 ttl=108 time=321.937 ms
64 bytes from 207.251.194.25: icmp_seq=5 ttl=108 time=323.091 ms
64 bytes from 207.251.194.25: icmp_seq=6 ttl=108 time=324.309 ms
64 bytes from 207.251.194.25: icmp_seq=7 ttl=108 time=321.500 ms
64 bytes from 207.251.194.25: icmp_seq=8 ttl=108 time=320.118 ms
64 bytes from 207.251.194.25: icmp_seq=9 ttl=108 time=318.527 ms

--- smtp.localnet.com ping statistics ---
10 packets transmitted, 10 packets received, 0% packet loss
round-trip min/avg/max/stddev = 295.292/326.904/375.391/19.827 ms"

Is this helpful information or just confusing miscellaneous data?

Thanks!

Jun 2, 2009 2:57 AM in response to spdsail

Mail would be expected to have created a new Outbox.mbox folder -- did it?

Ernie

spdsail Author

Level 1

6 points

Jun 2, 2009 6:46 AM in response to Ernie Stamper

Mail did not initially create a new Outbox.mbox folder. When I "sent" the test messages the process was very quick and I did not see an Outbox. Based upon past observations of Mail, the Outbox was a transient item appearing when a message was to be sent and only lasting until the message was sent. I just created a new message with Mail offline. That allowed Mail to create a new Outbox folder.

This new Outbox seems to be "permanent". I sent another test message with the hope that the old Outbox was the source of my problem. Unfortunately, that did not prove to be the situation. The test message did not arrive at my work e-mail account nor did I receive the copy to my Corecomm voyager.net account.

Jun 2, 2009 7:07 AM in response to spdsail

Although not seen in the Sidebar to the Mail window, unless a message fails to send or is a long time sending, the Outbox.mbox folder is meant to always be in the Mailboxes folder of the Mail folder -- was that where you found it, and where the current version resides?

In Mail Preferences/Accounts/Account Information click on the arrows beside the name of the SMTP and choose Edit Server List. Once there click on the Advanced tab -- what are the settings you are using there? If Use Default Ports is selected, change to Use Custom Port, and enter Port 25, do not select SSL, and then enter Username and PW. While this does not seem to be a failure to connect, this may be worth trying.

Ernie

spdsail Author

Level 1

6 points

Jun 2, 2009 8:36 AM in response to Ernie Stamper

My mistake with regards to the Outbox observation. I was looking only at the Outbox icon in the sidebar and not the Outbox.mbox folder in the Library. The Outbox.mbox folder WAS recreated in the Library after sending a message. I noticed after recently quitting Mail, the Outbox icon in the sidebar did not reappear when I relaunched Mail. The Outbox icon appears as needed - which you explained is normal

With regards to the Edit Server changes you suggested, I made the changes and tried sending a message. However, smtp.voyager.net would accept authentication and I had to select "None" under authentication to be able send the message via port 25. The message was handled as before transferring to my Sent folder but never appearing in the intended e-mail accounts.

Thanks for the suggestion but the problem continues.

Jun 2, 2009 9:15 AM in response to spdsail

Very odd -- Corecomm instructions for both Entourage and Apple Mail say that Authentication is required on the Outgoing Server, and that for Entourage clearly shows use of Port 25. Please review those you have for Entourage which you report to be working?

What were the setting for Port for the Outgoing Server prior to your changes?

Ernie

spdsail Author

Level 1

6 points

Jun 2, 2009 9:34 AM in response to Ernie Stamper

The Corecomm instructions on their website for Apple Mail are out-of-date per their technical support group. When I tried to follow them I had serious problems prompting a call to Corecomm. The settings I am using are per phone conversations with the tech support group. I have suggested several times that they need to update the website information. You can see the results ...or lack thereof.

I used the same settings for Entourage

Before the change you suggested I was using the default port setting and no authentication.

Jun 2, 2009 12:15 PM in response to spdsail

Variation on a theme: I have a large number of Rules that redirect incoming messages to various staff (w/in the same domain), depending on which account they're addressed to. (e.g. Sales@, Support@, etc.) In a list of incoming messages, Mail places a jagged arrow next to certain emails, indicating a redirect has been executed on those messages that met the Rules.
Recently the intended recipients have not been receiving all of the redirects. I've asked our ISP to see if some strange new spam cop at the server level is filtering our mail. In the meantime, the big question:
Does any body know how I can see what action actually took place? (Redirects don't appear in the Sent folder)
Thanks in advance for your help.

Jun 2, 2009 3:14 PM in response to spdsail

And are they saying they are out-of-date for Entourage setup as well?

Since there is no message announcing failure, I was not expectant that the change in Port or authentication would matter.

I continue to believe that the SMTP is simply diverting your messages to oblivion, or somewhere, but I keep trying to devise a test that will prove it.

I would suggest composing a message with a rather large attachment, getting Corecomm on the phone, and have them watch as you proceed to Send. The large attachment should lengthen the time available for monitoring what is going on.

Ernie

spdsail Author

Level 1

6 points

Jun 2, 2009 5:30 PM in response to Ernie Stamper

I did not specifically ask if the settings shown on their website for Entourage are out-of-date. However, I suspect they are because you found reference to the need for authentication and Corecomm told me it was no longer necessary for Apple Mail. I used the same settings for Entourage that I received verbally for the Apple Mail program. Those settings worked for Entourage but not for Mail. Because Entourage worked, I did not try sending with Authentication required.

I will do as you suggest in your most recent post and try to send a message with an attachment and ask Corecomm to monitor. Thanks!

Jun 2, 2009 5:44 PM in response to Ernie Stamper

I've been having this same issue (sort of). I send an email. It looks like it's going. But later there is no message in the Send folder and my message never arrives. This happens periodically. I notice (when it seems to happen) that the computer isn't downloading new mail regularly. When I force quit (often have to) Mail the new mail loads and I'm able to send (and receive) mail again.

I hate not knowing if my mail is delivered. I have to check back in the Send folder to see what went and what didn't.

spdsail Author

Level 1

6 points

Jun 2, 2009 6:00 PM in response to spdsail

I created an e-mail message approaching the maximum file size allowed (about 9 Mb) and called Corecomm tech support and asked them if they would monitor while the message was being transmitted. The reply was not good. They told me they have no way of monitoring activity on an individual account or determine if a message is handled on their server either in real time of after the fact. That closes that opportunity.

They repeated their statement that there is no problem on their end; because my program settings are correct the problem must be with my program because other users of Apple Mail have no issues using Corecomm. They again encouraged me to choose another e-mail client software.

spdsail Author

Level 1

6 points

Jun 4, 2009 6:19 AM in response to spdsail

Here is an interesting observation from an experiment I conducted. I configured Apple Mail to send messages via my work account at verizon.net. I was successful in sending messages using Apple Mail via the verizon.net account and received copies at both voyager.net and verizon.net. I again tried sending a message using Mail via my voyager.net account but did not receive copies sent to either my verizon.net account or to my voyager.net account.

To me this indicates that Mail is capable of sending messages. The conundrum is Mail does not allow me to send new messages or respond to messages via the voyager.net (Corecomm) account. The fact that MS Entourage is capable of sending messages via my voyager.net account had suggested the problem was with the Apple Mail program. With my latest experiment, however, it appears there is something unique with how Mail and the Corecomm server interact.

I have again checked my settings and they are as specified by the Corecomm technical support group. Why would Corecomm's server have a problem processing messages from my Mail program?

Corecomm's technical support group tells me other Apple Mail users have no problems using Corecomm and that my Mail program must be defective. They have also stated though that many users of Apple Mail have varying problems and encouraged them to use another program like Thunderbird. I would want to avoid changing e-mail client programs if I can.

spdsail Author

Level 1

6 points

Jun 5, 2009 11:14 AM in response to Ernie Stamper

Ernie,

I contacted Corecomm and told them I was able to send a message through another ISP server using Apple Mail. (Please refer to my last post). That captured their attention and they are working with me to determine where the problem occurs when I send messages via their server(s). They had me send a large message to e-mail accounts they can access using both Apple Mail on my computer and via the Corecomm webmail site. That is similar to the test you suggested earlier this week. I will let you know what develops.

Thanks for all your time and efforts.

Jun 6, 2009 8:33 AM in response to spdsail

Thanks for this update, and I hope a solution develops. I thought they originally were arrogant to both dismiss Apple Mail, and then say lot's of other people could send with it. Obviously they took the track of thinking you didn't know what you were doing. I am glad alerting them to the fact that you could send with Mail from another account got them more "on the ball" but it should not have taken that to make them be more responsive.

Keep me posted -- I am doing a lot with family this weekend, so may be less responsive in reading the Discussions.

Ernie

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Mail deception - says messages are sent out but are not delivered