Confusing mail problem

Question

Confusing mail problem

I have four mail accounts in use in mail.
MAC, NCF, GMAIL and YAHOO.

When I send an E-mail from myself@gmail.com to myself@gmail.com it works.

When I send an E-mail from myself@mac.com to myself@mac.com, it fails, a dialog box comes up stating that I "Cannot send message using the server smtp.me.com:myself"

When I send an E-mail from myself@mac.com to myself@gmail.com it works.

When I send an E-mail from myself@mac.com to myself@gmail.com it fails, I get a message back that says in the message as shown below the line of dashes. There seems to be some confusion on Mails behalf about the addressing.

What can I do to fix this?

Note the From field oddity, "From: "Mr. Richard Tomkins" <richard.tomkins(at)gmail(dot)com>

--------------------------------------------------
richard_tomkinsr(at)mac(dot)com

Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 550 550 5.1.1 unknown or illegal alias: richard_tomkinsr(at)mac(dot)com (state 14).

----- Original message -----

Received: by 10.224.63.133 with SMTP id b5mr1846069qai.296.1261078484204;
Thu, 17 Dec 2009 11:34:44 -0800 (PST)
Return-Path: <richard(dot)tomkins(at)gmail(dot)com>
Received: from ?192.168.126.101? (i209-195-109-254.cia.com [209.195.109.254])
by mx.google.com with ESMTPS id 5sm6221835qwg.8.2009.12.17.11.34.43
(version=TLSv1/SSLv3 cipher=RC4-MD5);
Thu, 17 Dec 2009 11:34:43 -0800 (PST)
Message-Id: <11E06213-A8A1-48F5-94DC-EC4979A44C89@gmail.com>
From: "Mr. Richard Tomkins" <richard(dot)tomkins(at)gmail(dot)com>
To: Richard Tomkins <richard_tomkinsr(at)mac(dot)com>
Content-Type: text/plain; charset=US-ASCII; format=flowed
Content-Transfer-Encoding: 7bit
Mime-Version: 1.0 (Apple Message framework v936)
Subject: test
Date: Thu, 17 Dec 2009 14:34:41 -0500
X-Mailer: Apple Mail (2.936)

test

PowerBook G4, Mac OS X (10.5.8), Mixed network, Windows Servers, DNS, Wired and Wireless clients

Posted on Dec 17, 2009 11:39 AM

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Answer 1

Jun 26, 2017 5:23 PM in response to Community User

Actually, note the From field and To field oddities. Clearly these two entries are reversed. I tried this a number of times to ensure I was selecting the proper From and To and I don't understand.

How can I fix this?

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Answer 2

Jun 26, 2017 5:23 PM in response to Community User

Each of my accounts has the incoming and outgoing mail servers set as follows and in addition, each has the box Use only this server checked on.

So, I do not understand when you say I have the account names and servers mixed up.

Is there something going on here that I am confused about?

Thank you for your help.

MobileMe IMAP
mail.mac.com and smtp.me.com
NCF
mail.ncf.ca and mail.ncf.ca
GMAIL
pop.gmail.com and smtp.gmail.com
YAHOO
pop.mail.yahoo.ca and smtp.mail.yahoo.ca

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Answer 3

Jun 26, 2017 5:23 PM in response to Community User

Well, given that my accounts are all set up properly, see my previous post and that when composing an email one can choose the from field, it would seem that there is a bug within mail on 10.5.8.

My research has shown that everyone with multiple mail accounts experiences this same problem, the mail is always sent from the wrong address.

Time for Apple to look inside the code and fix a problem. This is a serious issue as it would appear to filtering and spam systems as s spam message when in fact it is legitimate.

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Answer 4

Jun 26, 2017 5:23 PM in response to Community User

I wanted to post a couple of pictures but, that appears to not be allowed.
I sent an email to richard_tomkins@mac.com from richard_tomkins@mac.com.
After I pressed the send button a message dialog was presented reading,
"Cannot send message using the server smtp.me.com:richard_tomkins, Verify ..., Select a different ..., Sending from <richard_tomkins@mac.com> ...

Given the above, can you discern what is wrong with my email addressing?

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Answer 5

Jun 26, 2017 5:23 PM in response to Community User

Connection Doctor, which I have run, many, many times, even before I started the original posting always says, and just now again says, everything is fine.

My repeated last post, also gives insight to the fact that for each account, I have always had and still have the checkbox checked on that say "Use only this server", which would prevent mail from being sent from the wrong server for the wrong account. After all, most reputable ISP's do not allow a user to send mail from a smtp server outside their domain.

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Answer 6

Jun 26, 2017 5:23 PM in response to Community User

Can you re-run your tests?

Connection Doctor says all is fine, all green buttons.

Before, you said:
When I send an E-mail from myself@gmail.com to myself@gmail.com it works.
When I send an E-mail from myself@mac.com to myself@mac.com, it fails
When I send an E-mail from myself@mac.com to myself@gmail.com it works.
When I send an E-mail from myself@mac.com to myself@gmail.com it fails

So, when you send an e-mail from myself@mac.com to myself@gmail.com, does it succeed or fail?

Sending an email this way worked this time.

What happens when you send e-mail from myself@gmail.com to myself@mac.com?

Sending an email this way resulted in the following mail posting from GMAIL. It never got to the .MAC account.

Delivery to the following recipient failed permanently:

richard_tomkinsr@mac.com

Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the recipient domain. We recommend contacting the other email provider for further information about the cause of this error. The error that the other server returned was: 550 550 5.1.1 unknown or illegal alias: richard_tomkinsr@mac.com (state 14).

----- Original message -----

Received: by 10.224.115.22 with SMTP id g22mr7909500qaq.6.1262055756350;
Mon, 28 Dec 2009 19:02:36 -0800 (PST)
Return-Path: <richard.tomkins@gmail.com>
Received: from ?192.168.126.101? (i209-195-114-209.cia.com [209.195.114.209])
by mx.google.com with ESMTPS id 20sm10968167qyk.5.2009.12.28.19.02.34
(version=TLSv1/SSLv3 cipher=RC4-MD5);
Mon, 28 Dec 2009 19:02:35 -0800 (PST)
Message-Id: <6544DE7F-F311-41E2-9E87-183C0F5A1F37@gmail.com>
From: "Mr. Richard Tomkins" <richard.tomkins@gmail.com>
To: Richard Tomkins <richard_tomkinsr@mac.com>
Content-Type: text/plain; charset=US-ASCII; format=flowed
Content-Transfer-Encoding: 7bit
Mime-Version: 1.0 (Apple Message framework v936)
Subject: test 2
Date: Mon, 28 Dec 2009 22:02:32 -0500
X-Mailer: Apple Mail (2.936)

test 2

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Answer 7

Jun 26, 2017 5:23 PM in response to Community User

After going over the failing email again and again, I see now that the actual email address is wrong. Event though I chose the email address from a dialog box, the email address that MAIL used was in fact an alias, or rather, a Previous Recipient.

I have just found Previous Recipient listings in MAIL and it would appear that I must clean up all the bad stuff in there, including an entry for myself that is wrong.

I say thank you to etresoft for standing by so patiently and helping me to figure this problem out.

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Answer 8

Jun 26, 2017 5:23 PM in response to Community User

Further to this topic,

The bad Previous Recipient alias continued to exist in Address Book and had to be deleted from there. I do not know which one populated the other, mail to address book or address book to mail, but the badly formed email address was in both applications.

Possibly, the many other people experiencing this problem have a similar problem, a bad email alias (aka Previous Recipient).

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Answer 9

Jun 26, 2017 5:23 PM in response to Community User

Anybody out there???????????

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Answer 10

etresoft

Level 9

57,212 points

Dec 24, 2009 5:18 PM in response to Community User

richard_tomkins wrote:
Actually, note the From field and To field oddities. Clearly these two entries are reversed. I tried this a number of times to ensure I was selecting the proper From and To and I don't understand.

How can I fix this?

It looks like you have the account names and servers mixed up. You have to make sure that the gmail account with your gmail address uses the gmail server for both sending and receiving. The same is true for mac.com. Both the sender and receiver at mac.com must match the mac.com e-mail address.

That would explain why you are getting that message with the From and the To fields "reversed". I don't think they are reversed at all. You tried to send from gmail to mac.com and Google said it couldn't deliver it because your mac.com address is invalid or incorrect. Whatever you have wrong with the mac.com address would also explain why you are unable to use that account to send e-mail.

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Answer 11

etresoft

Level 9

57,212 points

Dec 26, 2009 8:26 AM in response to Community User

richard_tomkins wrote:
Is there something going on here that I am confused about?

You need to make sure your e-mail addresses are matched up with the correct server. If your "from" address says gmail, you must use the gmail server. If your "from" says mac.com, you need to use whatever mac.com/me.com is. If one of these SMTP server is poorly configured, it might work anyway and that could cause confusion.

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Answer 12

etresoft

Level 9

57,212 points

Dec 27, 2009 3:46 PM in response to Community User

richard_tomkins wrote:
Well, given that my accounts are all set up properly

I don't think so, considering you can't send e-mail successfully.

when composing an email one can choose the from field, it would seem that there is a bug within mail on 10.5.8.

This is a user to user tech support forum. I will be happy to help you resolve your problem if you meet me halfway. If you've already made up your mind and assigned blame appropriately, then there isn't anything else I can do.

My research has shown that everyone with multiple mail accounts experiences this same problem, the mail is always sent from the wrong address.

Your research is faulty. I have multiple e-mail accounts and I've never experienced this problem.

Time for Apple to look inside the code and fix a problem.

The problem is within your e-mail accounts, not Apple Mail.

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Answer 13

Jun 26, 2017 5:23 PM in response to Community User

OK, I would appreciate some assistance and will try to keep an open mind.

How are my email accounts not set up properly?

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Answer 14

etresoft

Level 9

57,212 points

Dec 28, 2009 12:49 PM in response to Community User

You have to make sure that when you send an e-mail address using gmail, your "from" address is gmail. When you send an e-mail address using mac.com, your "from" address is .mac/me or whatever.

Your example is an e-mail message from gmail to .mac com. Plus, it looks like your .mac e-mail address might not be correct.

It would be helpful to run Mail's diagnostics and your original set of tests. Here is what you posted:

When I send an E-mail from myself@gmail.com to myself@gmail.com it works.
When I send an E-mail from myself@mac.com to myself@mac.com , it fails
When I send an E-mail from myself@mac.com to myself@gmail.com it works.
When I send an E-mail from myself@mac.com to myself@gmail.com it fails

Clearly, there is a serious discrepancy here. If you can clear that up and clearly list under which conditions it works and fails, it would be very helpful. Plus, make sure that when sending from mac.com, you are using a mail.com "from" address. If your "from" e-mail address doesn't match the SMTP server, then it should fail.

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Answer 15

etresoft

Level 9

57,212 points

Dec 28, 2009 4:20 PM in response to Community User

richard_tomkins wrote:
I wanted to post a couple of pictures but, that appears to not be allowed.

Your e-mail content is irrelevant.

I sent an email to richard_tomkins@mac.com from richard_tomkins@mac.com .
After I pressed the send button a message dialog was presented reading,
"Cannot send message using the server smtp.me.com:richard_tomkins, Verify ..., Select a different ..., Sending from < richard_tomkins@mac.com > ...

Given the above, can you discern what is wrong with my email addressing?

No. It looks like either your name and/or password for mac.com is incorrect. I know they recently changes from .mac to mobile.me, so you need to double-check your server settings.

What does Mail Diagnostics report?

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