My Mail suddenly rejects outgoing with message Authentication required

I don't know what happened to the prvios bit of background I've provided - don't seem able to see it any more
However
I HAVE NOTIVED SOMETHING
My "Account Info" in Mial has a box asking for TLS certificate - whereas my partner's email (which is giving no proiblems) doesn't
At present this is on the choice NONE
there is an alternative which begins co.apple.appleid.prd. then a long list of numbers
Could this be relevant?
Hope someone can understand this and offer a pointer to help?
Or should I try chat or telehone support?

a proxy is a server that protect user in the network from internet, filther request with personalised parameter
can also reduce internet trafic by saving locali the most visited website so insted of loading from internet a million time it load it from the proxy
for more detail http://en.wikipedia.org/wiki/Proxy_server
you can go to your router seting see if your build-in proxy is activated
if yes desactivate it and save/apply

Similar Messages

When trying to launch iTunes it freezes and I get the message: "Authentication Required. To access this site you need to log in to area "100656 on mellor.co. Your password will be sent in the clear." I am unable to enter a uname or password. Please help!!

When trying to launch iTunes on my PC running Windows 7 it freezes and I get the message: "Authentication Required. To access this site you need to log in to area "100656 on mellor.co. Your password will be sent in the clear." Because iTunes is frizen at this point I am unable to enter a username or password, or in fact do anything. Please help!! I have uninstalled and reinstalled iTunes numerous times as well as attempting all of the fixes that I could find on-line and still no joy.

That sounds extremely phishy to me... iTunes does not require authentication simply to launch it. I suspect you've got something nasty intercepting network traffic. That server may be set up to log the Apple ID that you enter so it can be used fraudulently. Try ComboFix from Bleeping Computer.
FWIW the domain mellor.co is registered to an accountants in Knutsford, Cheshire, UK, and produces the same authentication request if visited with a browser. There is no sign of a "real" publicly visible website at that domain which is a somewhat odd.
tt2

Outgoing mail suddenly rejected by ISP

since 5/6 days my outgoing mail is rejected by ISP and stays in the outbox after all worked fine for several month.
Browsing the internet like being here..... receiving mail from a different account all works fine, through the same wireless ISP connection, which suddenly rejects my outgoing mail.
here are some screenshots
confusing is that Airport Utilities can't find any wireless devise , even so I am using it, see screenshot
can somebody help????

I could sort my e-mail out today, the problem, was with the ISP new setting arrangement
about, there are two questions left :
b) Also why I was using the TPG wireless internet connection on the 02.05.2011 @ ca.1150pm, my macbook pro brought up a message like"somebody is using your (my computers) IP address, the settings changed". Can you make any sense of this or explain, what has happened???
c)Also, when I bring up my 'Airport Utility', while I am connected to TPG and even actively browsing the net on wireless it say's " it can't detect wireless devices (see screen shot above)

I changed nothing in my email account but can no longer send emails on my talktalk account and get the message, "authentication required." I am running Mavericks on my MacBook Pro. I can receive messages on talktalk. Can send

I changed nothing in my email account, talktalk.net, but can no longer send (server's response, "authentication required) No problem receiving, I am using Mavericks on my MacBookPro. No problem using Cloud, but I want to use my talktalk account as before the problem
I can send and receive using talktalk without any problems using my iPod and iPad.
I would be most grateful for help - in simple form, please, I am an 80 plus female Mac lover!

Hello Hazel139,
I found this in one of the similar post hope it helps you.
Level 6 (14,190 points)
X423424X
This helped meRe: Problem SENDING email Jun 17, 2012 1:40 PM (in response to Casanewton)
The error I see is you did not specify the proper authentication for the smtp server.
In the Mail preferences for the account, smtp popup, select Edit SMTP Server List. A sheet will drop down. Select Advanced tab on that sheet. You should, I assume, set the Authentication to password, and set the proper username and password. That's where the poper would be set if 587 is not the one you should be using. Maybe it is. I only bring it up since I see it trying to use port 587.
If you got this stuff already set correctly then I don't know. Mail has a problem in your setup. Maybe delete the account and recreate it from scratch.
https://discussions.apple.com/message/18670442#18670442

Sudden account problem with messages account

After a internet connection problem this morning (maybe not related) Messages asked for my account password. I typed it and it was rejected. This is an old account: [email protected] As you see, very old!I went to the AOL web site and could sign in ok. I donwloaded the AOL chat software and created the account. It worked fine!
I deleted the accoount in Messages and remade it. still password is rejected. I deleted it again and tried maing it from the System Preferences Internet account. This time it seems to make the account but then give an Unknow Error message!
Any ideas?
Cheers

Hi,
In the Message Received sound drop down have you tried changing the Sound ?
Can you hear it in Messages ?
It should show the default sound (the one from the app), the System Sounds and, if you have any, the User's Sound folder (~Library/Sounds).
To look in ~/Library /Sound open any Finder window and then use the Go menu whilst holding down the ALT key.
Select the Library from the Menu and navigate to the Sounds folder.
The app plays these sounds when you test and Select them.
However during normal use they are played by System Preferences > Sound > Sound Effects like a System Alert.
The Volume selected here has a bearing.
There have been issues reported with the Message Received sound playing during normal use when the app is no longer the app in focus. (not the "front" app)
Changing the Sound seems to help and more so if it is in ~/Library/Sounds.
Can you also use the Open Script Folder and deliberately run the AppleScript from there and have someone text you ?
Most of the above will check the Sound plays and the general Ability for the app to action Messages Received.
However the last paragraph should check out that the Script is working (That Apple Script itself works).
7:40 pm Saturday; March 22, 2014
 iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

Mail suddenly stops sending out messages.

I use Mail with Snow Leopard. I have 3 email accounts: U-verse, MobileMe and godaddy.com. Up until last week everything worked just fine. Then Mail stopped sending out messages on all three servers. They just sit in the Outbox. I can receive messages OK. I can go online and use the associated webmail sites. Connection Doctor gives me green dots on all accounts. Have not changed any settings although I did confirm they are configured properly. What the heck is going on?

That means nothing is wrong with Mail itself. The problem lies in your data. Mail is a very complex application with a lot of files. Rather than going through a long diagnostic process, I suggest you make a record of all your account settings, quit Mail, move your Library/Mail folder to the Desktop, delete the file Library/Preferences/com.apple.mail.plist from your home folder, and start over with a clean slate. Set up your accounts as if for the first time, test, and if all seems well you can restore your messages either from Time Machine, if you use it, or by importing them from the old Mail folder (File > Import Mailboxes...). It will take some work, but I don't know of an easier way. Make sure you have backups of everything before you start.
If you do use Time Machine, you have the option of restoring all the Mail files from a snapshot that predates the issue, but then you'll also have to find and restore the messages created since that time.

Why does mail suddenly import thousands of messages again?

Once every few months Mail under 10.6.8 re-imports 2700 or so emails and takes half an hour, but when finished it has not added anything I see in the mail list.
Specifically there are no "new" email messages. This has been going on for years.
2010 MacBook Pro w/10.6.8
Why is it doing this and is anything wrong somewhere?
TIA

This is my web setting for gmail
Notice what is checked. Now my corresponding Mac Mail sidebar
All mail is a hodpodge. I would not turn that on or (as you can see) even let it be shown.

550 5.7.1 RESOLVER.RST.AuthRequired; authentication required

Following error i get when sending mail to SharePoint mail enabled library. It create contac with non ruted domain. Domain is not public. Let say that ending of domain is LOC. So it is not
registered public domain…
And it is A contact, not Distribution group. Let put it , that that name of the contact is : [email protected]
I have setup Hybrid. All Exchange server s are Exchange 2013 CU5.
To make it work, I have tried to send mail, to that library through share mailbox or transport rule…. Every time I send mail from outside organization or from mailbox, that is hosted in O365 I get following error :
[email protected] <- I did use   email of shared mailbox , but that is returned
Your message can't be delivered because delivery to this address is restricted.
Diagnostic information for administrators:
Generating server: MBX01. noreg.loc
[email protected]
Remote Server returned '550 5.7.1 RESOLVER.RST.AuthRequired; authentication required'
Massage tracking loge, gives me following error :
RunspaceId              : 9fd72017-0941-42f0-8625-b58b1c79b367
Timestamp               : 6/12/2014 3:30:03 PM
ClientIp                :
ClientHostname          : MBX01
ServerIp                :
ServerHostname          :
SourceContext           :
ConnectorId             :
Source                  : ROUTING
EventId                 : FAIL
InternalMessageId       : 20190641259111
MessageId               : <[email protected]ngelabs.com>
Recipients              : {[email protected]}
RecipientStatus         : {[{LRT=};{LED=550 5.7.1 RESOLVER.RST.AuthRequired; authentication required};{FQDN=};{IP=}]}
TotalBytes              : 10261
RecipientCount          : 1
RelatedRecipientAddress :
Reference               : {<91a7f625-60e6-4070-a834-b120d77d4c41@ MBX01.noreg.loc>}
MessageSubject          : test 1111
Sender                  : [email protected]
ReturnPath              : [email protected]
Directionality          : Incoming
TenantId                :
OriginalClientIp        :
MessageInfo             :
MessageLatency          :
MessageLatencyType      : None
EventData               : {[DeliveryPriority, Normal], [ExternalOrgIdNotSetReason, ]}
Additional Info :
Customer has internal domain whom FQDN is noreg.loc. They have SharePoint farm. Farm has several mail enabled document libraries.   Email enabled libraries has FQDN of sharepoint.noreg.loc. They have about
100 of those mail enabled libraries. When library is crated it create contact, that is
[email protected],
[email protected] , and so on...
Internal users can send mail to that SharePoint library, works. It has stopped working for those whose mailbox »user« is moved to Office 365.
Now i have a problem. Because domain noreg.loc and sharepoint.noreg.loc is publically non-rutable domain, i do not wont to change all emails addresses of library, I will or I`m trying to do workaround.
First detailed of contact :
[email protected]
External SMTP : [email protected]
Alternate email :
[email protected],
[email protected]
I can not use distribution group, and sync it to office 365. Because expansion of members in that distribution group, will happened in Office 365 Exchange server. That will end up with error non existing domain for
lsharepoint.noreg.loc.
So I have tried with shared mailbox, that has setup forward to contact
[email protected]. I know that shared mailbox, has pickup mail, because, I have forget to set it, that every one can send to these recipient. When that is setup, mail is received, and transferred to [email protected]
, where it failed with error authentication required. Server that   send error is Mailbox server “Exchange 2013”.
I will try to setup classical mailbox, with forward to contact, but that would use local licences, that I do not wont.
I need to setup default receive connector on MBX server to allow no-authenticated “server” to relay, which I thing is security problem.
I do not understand why would sending mail to contact, required authentication

Hello,
Please try to use telnet command to send message to sharepoint to check the result.
Please create a new receive connector, and then enable "anonymous users" on a new receive connector to check the result.
Cara Chen
TechNet Community Support

Webservice Header Issue ( Authentication required )

Dears I am developing client application to consume webservice, the webservice developer sent me the wsdl file and the sample SOAP request , all look fine for me
the issue that when I am trying to call the webservice it returns an error message ( Authentication Required ) but I am sending the user name and the password in the header as expected.
here is the Sample SOAP
<soapenv:Envelope xmlns:fax="http://fax.po.ws.apps.oracle.xxdof/" xmlns:soapenv="http://schemas.xmlsoap.org/soap/envelope/">
<soapenv:Header><wsse:Security soapenv:mustUnderstand="1" xmlns:wsse="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-wssecurity-secext-1.0.xsd" xmlns:wsu="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-wssecurity-utility-1.0.xsd"><wsse:UsernameToken wsu:Id="UsernameToken-5A2B82D9EE5888AE0414252886487322"><wsse:Username>weblogic</wsse:Username><wsse:Password Type="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-username-token-profile-1.0#PasswordText">weblogic1</wsse:Password><wsse:Nonce EncodingType="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-soap-message-security-1.0#Base64Binary">jMqFQqEM30Yp+t3tP+8meg==</wsse:Nonce><wsu:Created>2015-03-02T09:30:48.732Z</wsu:Created></wsse:UsernameToken></wsse:Security></soapenv:Header>
<soapenv:Body>
<fax:faxStatus>

<arg0>0</arg0>

<arg1>0</arg1>

<arg2>0</arg2>

<arg3>0</arg3>

<arg4>0</arg4>

<arg5>0</arg5>
</fax:faxStatus>
</soapenv:Body>
</soapenv:Envelope>"
and below the request I am sending
<s:Envelope xmlns:s="http://schemas.xmlsoap.org/soap/envelope/" xmlns:u="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-wssecurity-utility-1.0.xsd">
<s:Header>
<o:Security s:mustUnderstand="1" xmlns:o="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-wssecurity-secext-1.0.xsd">
<o:UsernameToken u:Id="uuid-90e0f212-3dc0-4913-96a8-175697d5240d-1" xmlns:u="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-wssecurity-utility-1.0.xsd">
<o:Username>username</o:Username>
<o:Password Type="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-username-token-profile-1.0#PasswordText">password</o:Password>
<o:Nonce EncodingType="http://docs.oasis-open.org/wss/2004/01/oasis-200401-wss-soap-message-security-1.0#Base64Binary">JY+mppXhcmr+Rl/kzURVoYKFKa4=</o:Nonce>
<u:Created>2015-03-18T09:43:26.248Z</u:Created>
</o:UsernameToken>
</o:Security>
</s:Header>
<s:Body>
<faxStatus xmlns="http://fax.po.ws.apps.oracle.xxdof/" xmlns:i="http://www.w3.org/2001/XMLSchema-instance">
<arg0 xmlns="">0</arg0>
<arg1 xmlns="">1</arg1>
<arg2 xmlns="">2</arg2>
<arg3 xmlns="">3</arg3>
<arg4 xmlns="">4</arg4>
<arg5 xmlns="">5</arg5>
</faxStatus>
</s:Body>
</s:Envelope>
Can you please point me what I am missing here
thanks
wasim

Hi,
In the Sample SOAP, the username and password are weblogic and
weblogic1. But the request you are sending are
username
and password which are not the authenticated account.
You need make sure that the username and password you passed are authenticated
account.

My macbook pro with OS 10.6.7 'mail' program does not send my mail through the IPS wireless, I am connected to. The message is my 'e-mail is rejected by the server'. It has been working until 5 days ago. The connection doctor says I am connected and no lo

My macbook pro with OS 10.6.7 'mail' program does not send my mail through the IPS wireless, I am connected to. The message is my 'e-mail is rejected by the server'. It has been working until 5 days ago. The connection doctor says I am connected and no log in required.
After trying lots I found now in 'Airport Utility is 'unable to detect any airport wireless devises.....'
There is no provider to be seen in airport utility and only 'rescan' is an option with no results...
even so I am connected and can browse the net receive mail etc. and the outgoing 'mail server' is set to the internet provider I am connected to.
Can you enlighten me what can I do I need to use my e-mail program urgently !!!
Thanks for your help

I'm not sure what "IPS wireless" is, but unless you have an Apple Wi-Fi base station (such as a Time Capsule, AirPort Extreme, or AirPort Express), AirPort Utility won't see anything.
You might try defining a new SMTP server to see if that will work any better.
By the way, the subject field for these messages isn't intended to hold a lot of text. Put a short description of your problem in the subject field and save the rest of your message for the body field.

When sending e-mail messages to a mail-enabled public folder that have been replicated from old Exchange Server 2000/2003/2007, Exchange Server 2010 environment mails are rejected with NDR.

Hi, I would like to share with you issue that I’ve solved regarding mail-enabled PF that migrated from Exchange 2000/2003/2007 to 2010, I’ve searched & contacted my MVP leader – there’s no official KB regarding this issue right
now, so I’m posting here in order to share this among others.
Note: There’s article(s) that talked about PF replication from Exch2000/2003/2007 to 2010 – this is the same issue as well.
Symptoms
E-mail messages that been sent to mail-enabled public folder in Exchange Server 2010 environment rejected with the following NDR:
“#< #5.2.0 smtp;554 5.2.0 STOREDRV.Deliver.Exception:ObjectNotFoundException; Failed to process message due to a permanent exception with message The Active Directory user wasn’t found. ObjectNotFoundException: The Active Directory
user wasn’t found.> #SMTP#”
Sometimes Exchange Server 2010 is documented as well Event ID 1020 on the Event Viewer with this information:
“Log Name: Application
Source: MSExchange Store Driver
Event ID: 1020
Level: Error
Description:
The store driver couldn’t deliver the public folder replication message "Hierarchy ([email protected])" because the following error occurred: The Active Directory user wasn't found.”
Cause
In an environment where Microsoft Exchange Server 2000 or Microsoft Exchange Server 2003 previously existed, and all those servers have been removed, there is a chance that an Administrative Group (First Administrative Group or another custom Administrative
Group) remains with a Servers container, but no servers inside it.
During replication, when the Exchange 2010 Store Driver sees the empty Servers container in Active Directory, it's expecting a System Attendant object inside the container and when it is not found the error occurs.
Resolution
To work around the issue, delete the empty Servers container. This can't be done through Exchange System Manager. Use the ADSI Edit tool to remove it using the following steps:
Warning If you use the ADSI Edit snap-in, the LDP utility, or any other LDAP version 3 client, and you incorrectly modify the attributes of Active Directory objects, you can cause serious problems. These problems may require you to reinstall Microsoft Windows
2003 Server, Microsoft Windows Server 2008, Microsoft Exchange 2010 Server or both Windows and Exchange. Microsoft cannot guarantee that problems that occur if you incorrectly modify Active Directory object attributes can be solved. Modify these attributes
at your own risk.
1.
Start the ADSI Edit MMC Snap-in. Click Start, then
Run, and type adsiedit.msc, and then click OK.
2.
Connect & Expand the Configuration Container [YourServer.DNSDomainName.com], and then expand
CN=Configuration,DC=DNSDomainName,DC=com.
3.
Expand CN=Services, and then CN=Microsoft Exchange, and then expand
CN=YourOrganizationName.
4.
You will see an empty Administrative Group. Expand the
CN=YourAdministrativeGroupName.
5.
Expand CN=Servers.
6.
Verify there are no server objects listed under the
CN=Servers container.
7.
Right click on the empty CN=Servers container and choose
Delete.
8.
Verify the modification, and try to send again the E-mail to the mail-enabled public folder.
Applies to
Exchange Server 2010, Standard Edition
Exchange Server 2010, Enterprise Edition
Netanel Ben-Shushan, MCSA/E, MCTS, MCITP, Windows Expert-IT Pro MVP. IT Consultant & Trainer | Website (Hebrew): http://www.ben-shushan.net | IT Services: http://www.ben-shushan.net/services | Weblog (Hebrew): http://blogs.microsoft.co.il/blogs/netanelb
| E-mail: [email protected]

Sounds like you are looking in the wrong Administrative Group container which is why you are seeing your Exchange 2010 servers in there.
When you install Exchange 2003 only you will see a container named by default as "CN=First Administrative Group" container. But this could be named anything if you changed the Organization Name on the installation when you installed the first
Exchange 2003 server into the domain/forest.
You will notice that when you install Exchange 2010 part of the AD setup is to create a new configuration container and is named by default "CN=First Administrative Group (FYDIBOHF23SPDLT)".
So it sounds like you are not looking in the right location within ADSIEdit.
You may find the following article also helpful for this issue which is the same resolution:
http://blogs.technet.com/b/sbs/archive/2012/05/17/empty-cn-servers-container-causing-issues-with-public-folders-on-small-business-server-2011.aspx
I recommend though that you ensure your Exchange 2003 servers are fully uninstalled or no longer present in your environment before you go deleting the Servers container though.. The following Microsoft article will help with this:
http://technet.microsoft.com/en-gb/library/gg576862(v=exchg.141).aspx

Mail: outgoing and now incoming mail server rejects password

Hello all. Hope you can help with this one.
I was using Mail as normal yesterday. I use the same incoming mail server and SMTP server (my university's Exchange server). Then sending mail suddenly failed. The error message I get is:
The SMTP server “exch.wlv.ac.uk” rejected the password for user “(null)”
Enter your password again or cancel.
The settings are port 995 for outgoing mail, using SSL and requiring password authentication.
I've verified my settings and passwords with IT support. They say they haven't altered anything, and nor have I.
I've tried Connection Doctor: it says Mail connected with the exch. server without any problems. However, under Account Information, the server says (offline).
I've changed ports (to 25 and 587): no success.
I've deleted my password from Keychain and Mail plist and reentered it. No success.
I've verified and repaired permissions.
I'm now not getting incoming mail either: the error message is
There may be a problem with the mail server or network. Verify the settings for account “Staff POP” or try again.
The server returned the error: The connection to host exch.wlv.ac.uk on port 25 failed.
I can send and receive using web-based OWA.
Is there anything else I can do, or is it a server problem?
Thanks,
Aidan

May be no help to you Aidan except comfort in numbers. Mail has started behaving erratically for me in the past week. My inbox and account mail has disappeared and my accounts keep being rejected by the webmail host similar to your problem; password rejected etc. Then Mail closes abruptly telling me there's a problem and offering to send a report to Apple. Mail is version 4.5 and the iMac is 10.6.8. Help!
Maurice

Why has mail suddenly started saying that my outgoing mail server is offline?

Why has mail suddenly started saying that my outgoing mail server is offline?
I can receive mail from my ISP using Apple Mail but as of this morning I can't send via my ISP.
When I check Mail preferences, they say that my ISP's outgoing mail server is "offline".
I haven't changed any settings, so what's gone wrong? I need a fix. At the moment I'm having to use Gmail.

If your email is hosted by Google then there are several known issues with Apple Mail under Mavericks accessing Gmail. Using a web browser is a good backup. In Apple Mail you can goto the menubar, choose Mailbox and choose take all accounts offline. Then bring them back online. Worst case you may need to delete and readd the account (usually if something was setup wrong) Menu bar - Mail > Accounts.
If you have turned on 2 step Google Authentication then you'll need to issue a specific email password for Apple Mail to use to bypass authentication. Google the steps.
Best of luck in getting your mail server online. Hopefully you can specify multiple servers in settings.

When I try to send e-mail I get an error message stating that the e-mail address was rejected by the server. When I send to e-mail from another address, I get back an error saying the e-mail address is unknown. My e-mail has worked fine for years until

When I try to send e-mail I get an error message stating that the e-mail address was rejected by the server. When I send to e-mail from another address, I get back an error saying the e-mail address is unknown. My e-mail has worked fine for years until yesterday. HELP!

The specific text of the error message is very important here — I'm not sure exactly you're encountering here.
If you're able to connect to your email server and are able send email to other email addresses and if the failures are specific to one email recipient address, then please contact the intended recipient of the failing email, and confirm their address is valid. (This is the way I'm reading your question.)
If you are unable to send any email to any other email addresses and this is specific to your email address, then try the web mail client interface (if one is available) to verify your login user and password, and check with your email ISP for assistance. If your email password works via web mail, follow this Apple troubleshooting guide, then — if everything else fails — I'd probably then entirely remove the email account from Mail.app and re-add it per your email ISP's particular setup requirements. (Some issue with the setup or maybe a corrupt setting in OS X or a problem at the mail ISP servers is a common problem, but this effects attempts to send to all email addresses via that account.)
An email account setup is specific to an email provider, unfortunately. If you're using one of the more common email ISPs, then there are usually setup guides and frequently-asked questions posted online.

Mail.app: Select outgoing (SMTP) server per message?

Dear community members,
I'm looking for a solution to the following problem:
I do have multiple e-mail accounts which are configured in the following way: One of them is the master account (let's say [email protected]) added to Mail.app as a POP account. The other ones (let's call them [email protected] and [email protected]) are on different servers and are configured to forward all incoming mail to [email protected] They are, however, not added to Mail.app as additional accounts. That is because it's not necessary for receiving mail with these addresses, since all incoming mail is forwarded to [email protected], anyway, and therefore immediately available in Mail.app.
The problem arises when sending e-mails within Mail.app. I can easily add all three addresses in the "Mail" > "Settings" > "Accounts" settings window by entering them in the e-mail-address-field separated by comma (e.g. "[email protected], [email protected], [email protected]“). This allows me to select the desired outgoing address on a per-message basis in the compose window.
There is, however, a problem with this: This setting means that mail from all three addresses is being sent using the same SMTP server. This can cause problems for domains that do have SPF-records, for example. Therefore, I'd very much prefer to not only select the outgoing mail address on a per-message-basis, but also the SMTP-server I'd like to use. Since Mail.app allows me to add multiple SMTP servers in the account's settings window, I believe there has to be a way to select which one to use on a per-message-basis? Whenever there's a problem with an SMTP-server, a window opens up asking me which of the alternative SMTP servers I'd like to use, instead. This indicates that this function exists – it's just far from obvious for me where to find it in a normal usage scenario.
Does anyone have an idea? Any hint is welcome!
Thanks
Nick

That has nothing to do with it. I ended up working around the problem by changing the account name.
But I still think this is a bug, so I won't mark the topic as answered (a workaround is not the solution).

My Mail suddenly rejects outgoing with message Authentication required

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