How to satisfy POP-before-SMTP outgoing authentication?

When using a third party email account (i.e. included with my website hosting account), I am unable to send email. The outgoing server auth method used on my host server is POP-before-SMTP. However, in the iphone settings, there are only 4 choices:[ MD5 C-R // NTLM // HTTP MD5 Digest // Password ] Having set POP or IMAP every 15 minutes is sufficient interval to satisfy ... no problem there ... there doesn't need to be a specific choice for pop-before-smtp, but there does not appear to be a way to choose NO authentication at all for SMTP?
(i.e. with some computer email programs which do not support POP-before_SMTP, we turn outgoing authentication to OFF and ensure that email is retrieved on a regular schedule < 20 minutes, and all works perfectly.) For example, the Android Xperia has a NONE setting for SMTP auth.
There's no choice for either pop-before-smtp nor OFF on the iphone.
Can anyone suggest an app [or is it possible to hack] that would give us this functionality ?
We know we could use our carrier's SMTP, but we want BOTH our incoming/outgoing mail handled on our hosting server.

So, I've set SSL as "required", and also set CRAM-MD5, and basically I can see now that I can't receive any emails.
This really is one of the areas in which the Server Admin GUI lets you down.
If you set SSL as required, many remote servers won't be able to talk to you because they don't talk SSL by default. To enforce SSL for your users you really need a second port that forces SSL in addition to the standard port that doesn't.
You can do that, but only by delving in to Postfix's configuration files.
However, I've gotten something strange - I thought SMTP over SSL should default to 587. Why is it defaulted to 25 still? Do I need to add 587 somewhere else or something?
Ahh, the joys of ports.
There are two methods of implementing SSL with SMTP. One is SMTPS (which runs on port 465), the other is via TLS which uses the standard SMTP port. The difference is that SMTPS encrypts the entire connection (similar to HTTPS vs. HTTP), whereas TLS starts off with a non-encrypted connection and switches to secure once both client and server agree to use it (the client identifies itself, the server states it can use TLS, the client initiates a TLS session).
TLS is the model supported by Postfix, and that's why you still use port 25
Port 587 is the submission port. The line between 25 and 587 is pretty blurry, but many people implement different access controls and/or process rules for port 587 and have local users use that, leaving port 25 for non-local mail. Both ports can support TLS but you need to get under the hood to configure it.

Similar Messages

Pop before smtp and smtp auth

Hi Jay,
hope all is well with you.
what is pop before smtp and how to see if it is enabled?
what is smtp auth and how to see if it is enabled? Is it enabled by default on MS 6.x?
what happens if smtp auth is not enabled? Will my mail server be a relay?
Is there any additional configuration that should be done on messaging server to allow connection for dial-up users?
thanks,

Hi Jay,
hope all is well with you.
what is pop before smtp and how to see if it is
enabled?Pop before SMTP is a very old, and little used method for "authenticating" users. There is virtually no reason to turn this on, anymore.
It's done through the MMP, and is the only reason to actually use the SMTP proxy that's part of MMP.
I would not go there unless your environment requires it. Most do not. Most clients support SMTP authentication, which is much better, and is on by default.
>
what is smtp auth and how to see if it is enabled? Is
it enabled by default on MS 6.x?See above. Yes, smtp authentication is on by default.
>
what happens if smtp auth is not enabled? Will my
mail server be a relay?Totally different issue.
No.
If smtp auth is off, if you have external users, they likely will not be allowed to send to other external users..
>
Is there any additional configuration that should be
done on messaging server to allow connection for
dial-up users?If "dial-up users" means that they come from ip addresses outside your network, then smtp auth will allow them full access.
thanks,

Pop before SMTP

Hi Guys,
I've recently moved from my Linux Mail Server to Leopard Server, and am now experiencing issues sending mails from outside my internal LAN.
Basically, I get the message: NOQUEUE, RCPT - relay access denied. I believe it's because it doesn't know that I am a trusted machine, and thus rejects the relay.
In an attempt to fix this problem, I had to get POP before SMTP installed as a workaround on the Linux machine few years back.
Any ideas on how I can change this with Leopard Server? Should I enable SSL? Should I enable MD5 Password or something? Or do I still need to install POP-before-SMTP?
Thanks for all your kind help in advance.

So, I've set SSL as "required", and also set CRAM-MD5, and basically I can see now that I can't receive any emails.
This really is one of the areas in which the Server Admin GUI lets you down.
If you set SSL as required, many remote servers won't be able to talk to you because they don't talk SSL by default. To enforce SSL for your users you really need a second port that forces SSL in addition to the standard port that doesn't.
You can do that, but only by delving in to Postfix's configuration files.
However, I've gotten something strange - I thought SMTP over SSL should default to 587. Why is it defaulted to 25 still? Do I need to add 587 somewhere else or something?
Ahh, the joys of ports.
There are two methods of implementing SSL with SMTP. One is SMTPS (which runs on port 465), the other is via TLS which uses the standard SMTP port. The difference is that SMTPS encrypts the entire connection (similar to HTTPS vs. HTTP), whereas TLS starts off with a non-encrypted connection and switches to secure once both client and server agree to use it (the client identifies itself, the server states it can use TLS, the client initiates a TLS session).
TLS is the model supported by Postfix, and that's why you still use port 25
Port 587 is the submission port. The line between 25 and 587 is pretty blurry, but many people implement different access controls and/or process rules for port 587 and have local users use that, leaving port 25 for non-local mail. Both ports can support TLS but you need to get under the hood to configure it.

POP before SMTP on SENDmail

Hi ,
I am trying to send out mails using sendmail, but the server requires SMTP authentication.
Does any one know , as to how this can be done.

So, I've set SSL as "required", and also set CRAM-MD5, and basically I can see now that I can't receive any emails.
This really is one of the areas in which the Server Admin GUI lets you down.
If you set SSL as required, many remote servers won't be able to talk to you because they don't talk SSL by default. To enforce SSL for your users you really need a second port that forces SSL in addition to the standard port that doesn't.
You can do that, but only by delving in to Postfix's configuration files.
However, I've gotten something strange - I thought SMTP over SSL should default to 587. Why is it defaulted to 25 still? Do I need to add 587 somewhere else or something?
Ahh, the joys of ports.
There are two methods of implementing SSL with SMTP. One is SMTPS (which runs on port 465), the other is via TLS which uses the standard SMTP port. The difference is that SMTPS encrypts the entire connection (similar to HTTPS vs. HTTP), whereas TLS starts off with a non-encrypted connection and switches to secure once both client and server agree to use it (the client identifies itself, the server states it can use TLS, the client initiates a TLS session).
TLS is the model supported by Postfix, and that's why you still use port 25
Port 587 is the submission port. The line between 25 and 587 is pretty blurry, but many people implement different access controls and/or process rules for port 587 and have local users use that, leaving port 25 for non-local mail. Both ports can support TLS but you need to get under the hood to configure it.

How to configure Mail to use different ports for POP and SMTP?

I am trying to configure Mail for my AT&T account. It requires me to configure POP (incoming) mail for port 995, and SMTP (outgoing) mail for port 465. However there doesn't seem to be an option to configure different ports for these. Is that correct, or am I missing something?
Alternatively can I configure two accounts, one for POP incoming and one for SMTP outgoing? My incoming POP account does work, but in configuring an outgoing account I still have to configure a POP server name and that will not work for the outgoing port.
Any advice on how to solve this would be appreciated.

Understand. It is really quite easy to do in Mail, too. Kappy told you how to set up the smtp piece. I gave you pop info. These two things are on different panels within Account Preferences.
To recap his and my posts
SMTP:
In Mail Prefs, click on the accounts icon. Click on your att yahoo account on the list. On the right of the window, in the lower portion, you see an smtp server menu. Open it and select edit. Select Edit Server, then click on its Advanced tab. Set up port 465 with SSL.
POP:
This is on a different panel in Mail PRefs Accounts. Now in Mail Prefs, click on the accounts icon. Click on your att yahoo account on the list. On the right of the window, you see three tabs, acc't info, mbox behaviors, and Advanced. This is where things are different than for smtp. You are going to configure stuff on a different "advanced" panel than where you were for the smtp stuff. Click on the advanced tab. There is a field for port with a SSL checkbox next to it and an authentication drop down menu. Check the box and it should quickfill change from 110 to 995. Autentication drop down is probably already default to password.
Did you visit the URL I gave you previously? It even gives you screen shots.

Dealing with two email accounts that use the same SMTP (outgoing) server

Folks:
re:   mail.app 5.2 (MacOS 10.7.4) with respect to POP accounts only
I've read this thread multiple times, spent many hours experimenting, and my web searches haven't come up with any more useful help.
How do you persuade mail.app to accept settings for two similar, but distinct email accounts that use the same SMTP (outgoing) server?   Say, the accounts are "blue.example.com" and "[email protected]". These have different user names and passwords.   The SMTP server is "smtp.example.com".
I think this is the appearance of success: the SMTP Server List (as seen in edit-the SMTP-Server-List mode) shows:
Server Name                   In Use By Account
    smtp.example.com      [email protected], [email protected]
(Description column omitted for brevity. And of course, mail.app doesn't show the little envelope icons.)
But I cannot reliably achieve this result.   When I select the SMTP server from the list for the second account --as suggested in the above-referenced thread--- I see the credentials (user name and password) for the first. Should I overwrite them? No, I don't think so -- I think that will break the first account.   I feel mail.app should present me with empty credentials boxes instead. Maybe this happens -- sometimes. But I can't see how to make it happen. Am I simply overlooking something?
A slightly different way of asking about this issue:   Suppose I manage to do a proper setup for the two accounts and they work. Then I change the password for "[email protected]" on the server. What is a reliable way of reaching the SMTP credentials for that account to make the edit? Same question for "[email protected]"?    Even when I successfully attach two accounts to one SMTP server, I seem only able to reach the first listed one to make changes. (In this case, "blue.example.com").
It is possible I'm missing something incredibly obvious...    I know the credentials for each account are distinct, but maybe mail.app copies them from the POP (incoming) settings.   Nah, that can't be, can it?   Or what?
Maybe I'm seeing bizarre things due to scrambled mail.app preferences. I've seen it before on other apps: delete the current preference file, get an auto-generated fresh one, and sanity returns. But with mail.app, with the prospect of losing years of emails --yeah, I've done it-- I'm extremely reluctant to mess around.
Suggestions, please.
TIA
Message was edited by: Hen3ry to clean up the table a little and add a parenthetical explanation.

OK, I'm convinced.   The mail.app UI is BROKEN -- in my primary user account. Such that it cannot reliably select an outgoing server for editing.
I created a new user account and installed some relevant example accounts in mail.app in that account. No problem. Well, a bit obscure, but still fully logical and reliable selection of individual SMTP accounts for editing.
For the sake of clarity, I think it is best to mark this "answered" and repost, focusing on the symptoms and asking how one might go about repairing the problem. So I'll do that.

IMAP, POP and SMTP information for manual email setup

How to manually set up your Telstra email service:
Telstra email on the BigPond platform
POP & SMTP
Your name
Enter your name as you’d like it appear in emails you send.
Account type
POP3
Incoming server details
Server address
mail.bigpond.com
Port
995
Encrypted connection
SSL
Outgoing server details
Server address
mail.bigpond.com
Port
587 or 465
Authentication
Yes
Encrypted connection
With SSL Encryption
Username
Enter your full email address (ending in '@bigpond.com' or '@bigpond.net.au')
Password
Enter your Telstra email account password which will be case-sensitive.
Other settings to check
Ensure the checkbox is ticked for Outgoing server requires authentication – in most mail clients, this is not ticked by default.
Use:
Secure Sockets Layer (SSL) with the POP and SMTP connection, and
SMTP authentication for security.
Ensure that your operating system and email client have the latest updates.
Telstra email on the Outlook.com platform
If you’re on the Telstra email platform with Outlook.com®, you can choose either of the following types of settings to set up email on your computer, tablet or mobile phone:
IMAP and SMTP
POP and SMTP
Where possible, it’s preferable to use the IMAP & SMPT settings as they provide an extra layer of security.
IMAP and SMTP
Your name
Enter your name as you’d like it appear in emails you send.
Account type
IMAP
Incoming server details
Server address
imap-mail.outlook.com
Port
993
Encrypted connection
SSL
Outgoing server details
Server address
smtp-mail.outlook.com
Port
587
Authentication
Yes
Encrypted connection
With TLS/STARTTLS (preferred) or SSL Encryption
Username
Enter your full email address (ending in ‘@bigpond.com’ or ‘@bigpond.net.au’)
Password
Enter your Telstra email account password which will be case-sensitive.
Other settings to check
Ensure the checkbox is ticked for Outgoing server requires authentication – in most mail clients, this is not ticked by default.
Use:
Secure Sockets Layer (SSL) with the POP and SMTP connection, and
SMTP authentication for security.
Ensure that your operating system and email client have the latest updates.
POP and SMTP
Your name
Enter your name as you’d like it appear in emails you send
Account type
POP3
Incoming server details
Server address
pop-mail.outlook.com
Port
995
Encrypted connection
SSL
Outgoing server details
Server address
smtp-mail.outlook.com
Port
587
Authentication
Yes
Encrypted connection
With TLS/STARTTLS (preferred) or SSL Encryption
Username
Enter your full email address (ending in '@bigpond.com' or '@bigpond.net.au')
Password
Enter your Telstra email account password which will be case-sensitive.
Other settings to check
Ensure the checkbox is ticked for Outgoing server requires authentication – in most mail clients, this is not ticked by default.
Use:
Secure Sockets Layer (SSL) with the POP and SMTP connection, and
SMTP authentication for security.
Ensure that your operating system and email client have the latest updates.
Outlook is a registered trademark of Microsoft Corporation in the United States and/or other countries.

Re: BigPond settings for POP, IMAP and SMTP
I am have trouble with Apple: they claim that because I have not physically changed my email address they won't "accept" it! (it's same one that I have had for the past 5years),
I am also unable to log on using the email address & password that I have for past 12 months!
Can I change my email address and password, when I have time (during business hours), regards Eric

IPad smtp outgoing mail server choices not shown.

I use one mail Gmail account to where all my other accounts forward their mail. This makes it simple for me to organize 10 different accounts.
In iPad Mail settings I've setup my main Gmail account with 10 other smtp outgoing servers but when I write an email I don't have the option to select which smtp server is used. In Apple Mail (Mac OS) this system works fine as they have the option to select whatever smtp servers are setup.
What is the point of having the option in the iPad to set multiple outgoing servers if you can not select which ones are used before sending?
I know I could setup various POP/IMAP accounts for each smtp I prefer to use but why make it so complicated and waste space and bandwith downloading duplicate messages?
Has anyone found a solution to this or am I missing something obvious?

Yeah, I don't know why the difference. Interestingly for me, the iOS version in iOS4.2 is "better" than the OSX version of Mail because now I can have more than one Exchange account.
I am sympathetic with your need to separate your lives. I have a client that accidentally got one of my alternate email addresses and cannot/will not update his address book with the "correct" address, despite my requesting several times over the course of a year. In any case, I don't think there is any way around this other than completely changing your email address. (If not a second Gmail, then Yahoo, Hotmail or other email provider.)
The only time I've ever seen a "no password" SMTP server was as I previously said, it used a "network authentication" method. Many, many moons ago, SMTP servers often didn't have password authentication so would often be used for spam relaying. Before mobile users, "network authentication" by ISPs was fine since they could figure out which user was spamming since they could trace the IP addr, MAC addr, etc back through the physical link to the user. But with mobile users who change networks constantly, the general trend was to password authentication, even for wired ISPs since their users would want to have access to send mail while away from home. (e.g.: you're a RoadRunner customer, but want to send mail while using your laptop on vacation in Italy.) This "prior authenticated download" I've never heard of anyone else doing.

How do I specify the gmail outgoing server if I have multiple gmail accounts in my mail? I have 2 business accounts and when I send mail from one account, it is sent from the other account and the sending email is not from the correct account.

I love my apple email and do not want to use google mail on safari. However, I have 2 gmail accounts set up on apple mail, but when I send mail from one of my gmail accounts (I choose the specific gmail account in the drop down window), it actually goes out as if it is from the other gmail account. I can't have that happen because one is my job, the other is a personal business account and unfortunately, the mail from both gmail accounts want to send through the personal business account. How do I make it send from a specific gmail account? I even tried deleting the accounts and setting them up again hoping I set it up wrong in the first place, but to no avail, it is still doing the same thing except this time I set the job account up first and then the personal business account and now everything goes from the job account! The only good thing is that the incoming messages work properly and they go into the correct inbox. Somebody please fix my outbox!

In Mail Preferences/Accounts/each GMail account, set up the SMTP Outgoing Server for each account separately, going into SMTP name/edit/Advanced and specify the Username of each account. The Outgoing servers must be two different servers, authenticated by the Username and Password of each.
Otherwise, the GMail SMTP server will change the from address to that of the account where the SMTP server was setup.
Ernie

Mail SMTP (outgoing) does not work after Yosemite upgrade

I have just updated Yosemite on my Mac and MacBook Air and the outgoing mails cannot be sent - the SMTP-connection fails.
It worked fully Ok few seconds before the upgrade was started.
So, I wonder if anyone or Apple can help on getting the Outgoing mails to work again.

For those of you having email password issues, I'd suggest:
1) Close your mail client (i.e. Apple Mail, Thunderbird, Outlook, etc).
2) Launch "Applications" > "Utilities" > "Keychain Access.app"
3) Select "login" from the sidebar top left area, then select "Passwords" in lower left area
4) Click into the Search box in the upper right and search for your ISPs server names. For example, type "aol" or "google" or "comcast", etc.
5) Look through the search results for password entries related to your SMTP (outgoing) or IMAP/POP (incoming) mail servers. Select them and delete them.
6) Open your email client and try to receive mail, and then to send mail. You should be prompted to enter your mail username and/or password.
Hopefully this might fix issues for those of you using mail clients that use Keychain for credential storage.

Sbcglobal SMTP Outgoing Mail

I ISP is sbcglobal and I want to send emails using my iPhone. These are the settings from sbcglobal:
[email protected]
pop.att.yahoo.com
smtp.att.yahoo.com
Outgoing mail server: Outgoing server (SMTP) requires authentication
Outgoing mail port #: 465, secure connection (SSL) checked
I can receive my emails through pop3 but I can't send any emails from my iPhone.
The error message I get is:
Cannot Send Mail
Check the account settings for the outgoing server
"smtp.att.yahoo.com"
OK

Brewgod23 - save yourself some headaches. You can actualy use the Y!Mail preset for ATT branded accounts (sbcglobal, att, etc). Following the instructions on this link will also give you "push" (most of the time) capabilities and IMAP where all of your online folders are synced with those on your iPhone.
http://helpme.att.net/article.php?item=11255

Dreamhost blocking SMTP outgoing email sent via MiFi 4510L hotspot

I've been using a MiFi 4510L as my only internet connection for about a year, and have been happy with it to date. Dreamhost.com is my email host (and web domain host).
I haven't been using the MiFi for a few days. Today I was unable to send any messages via the MiFi through Dreamhost's SMTP (outgoing email) server. This happens both when sending from my laptop's email client (Apple Mail) and also from my iPhone when WiFi (i.e. the Verizon MiFi connection) is enabled. It's not a mailserver authentication issue -- incoming email works, Dreamhost webmail send and receive works, and I can send from the (AT&T) iPhone with WiFi turned off (i.e. through AT&T's cellular network). I contacted Dreamhost support, who said:
- - - - - (begin Dreamhost response) - - - - -
DreamHost now performs spamhaus RBL look ups when using an smtp client such as Apple mail. This is to prevent spam from leaving our network. The issues you are describing is what happens when you attempt to send email from an internet service provider (ISP) that is on the spamhaus blocking list. Switching from wifi to 3g will change that IP address that we look up prior to sending the email. For the device that is blocked we can only recommend that you contact the ISP and ask them to either give you a different IP address or work to get their IP's delisted.
- - - - - (end Dreamhost response) - - - - -
I take this to mean that Verizon 4G LTE IP addresses have somehow been added to Spamhaus's database. Has anyone experienced this issue with sending email through a Verizon device using Dreamhost SMTP? What are my options?
Message was edited by: John Ciccarelli (New information: Dreamhost suggested using WhatIsMyIP.com to determine my IP address. It returned 166.250.33.162 and sure enough Spamhaus has that in its PBL and XBL lists. However, I'm using Authenticated SMTP (port 587), not the unauthenticated port 25. Are Verizon servers somehow listed on Spamhaus?)
Message was edited by: John Ciccarelli
More research: I repeatedly shut down and powered up the MiFi. Each time up, WhatIsMyIP.com returns a slightly different IP: 166.250.33.162, 166.250.32.186, 166.250.34.151, etc. Lookup shows these IPs are associated with vzwdomain.com or myvzw.com, not surprisingly. So presumably the MiFi gets mapped to a different actual IP each time it connects. The first of these 3 IPs showed up in Spamhaus's PBL and XBL lists; the other two just in the PBL list. Perhaps if I keep powering off/on it'll eventually connect via an IP that isn't on Spamhaus's list.

Are you using Mail app? You need to make sure the Outgoing Mail Server settings are exactly how your ISP recommends. So give them a call.

How to stop pop up in my macbook.

i am fed up with poping up new windows everytime i click on any link can anyone suggest me how to stop pop up in my macbook. i tried safari and google preference to block pop up but it's not working it out. thanks in advance...

You may have installed the "VSearch" trojan, perhaps under a different name. Remove it as follows.
Malware is constantly changing to get around the defenses against it. The instructions in this comment are valid as of now, as far as I know. They won't necessarily be valid in the future. Anyone finding this comment a few days or more after it was posted should look for more recent discussions or start a new one.
Back up all data before proceeding.
Step 1
From the Safari menu bar, select
          Safari ▹ Preferences... ▹ Extensions
Uninstall any extensions you don't know you need, including any that have the word "Spigot," "Trovi," or "Conduit" in the description. If in doubt, uninstall all extensions. Do the equivalent for the Firefox and Chrome browsers, if you use either of those.
Reset the home page and default search engine in all the browsers, if it was changed.
Step 2
Triple-click anywhere in the line below on this page to select it:
/Library/LaunchAgents/com.vsearch.agent.plist
Right-click or control-click the line and select
          Services ▹ Reveal in Finder (or just Reveal)
from the contextual menu.* A folder should open with an item named "com.vsearch.agent.plist" selected. Drag the selected item to the Trash. You may be prompted for your administrator login password.
Repeat with each of these lines:
/Library/LaunchDaemons/com.vsearch.daemon.plist
/Library/LaunchDaemons/com.vsearch.helper.plist
/Library/LaunchDaemons/Jack.plist
Restart the computer and empty the Trash. Then delete the following items in the same way:
/Library/Application Support/VSearch
/Library/PrivilegedHelperTools/Jack
/System/Library/Frameworks/VSearch.framework
~/Library/Internet Plug-Ins/ConduitNPAPIPlugin.plugin
Some of these items may be absent, in which case you'll get a message that the file can't be found. Skip that item and go on to the next one.
This trojan is distributed on illegal websites that traffic in pirated content. If you, or anyone else who uses the computer, visit such sites and follow prompts to install software, you can expect much worse to happen in the future.
You may be wondering why you didn't get a warning from Gatekeeper about installing software from an unknown developer, as you should have. The reason is that this Internet criminal has a codesigning certificate issued by Apple, which causes Gatekeeper to give the installer a pass. Apple could revoke the certificate, but as of this writing, has not done so, even though it's aware of the problem. This failure of oversight has compromised both Gatekeeper and the Developer ID program. You can't rely on Gatekeeper alone to protect you from harmful software.
*If you don't see the contextual menu item, 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.

CISCO CLEAN ACCESS AGENT ALWAYS POPS-UP EVEN ALREADY AUTHENTICATED

Hello,
Just wonder why clean access agent always pops-up even already authenticated. Please how can i eliminate those multiple pops-up?
thank you and best regards,
Edwin

Hi:
I have the same issue. Would you please tell me what you did exactly?
I am using OOB VGW mode.
NAC version is 4.7.2
Switch configurations:
snmp-server community RO RO
snmp-server community RW RW
snmp-server location LOCATION
snmp-server contact CONTACT
snmp-server enable traps snmp linkdown linkup
snmp-server enable traps mac-notification change move threshold
snmp-server host CAM_IP version 2c RW mac-notification snmp
mac address-table notification change interval 0
mac address-table notification change
mac address-table aging-time 3600

Mail down since Yosemite!! SMTP (outgoing)

hello everyone.. well I am in mexico city and I have problems with my outgoing mail since yosemite!!!
1st of all, I used to repair computers for 10 years so I thought I was able to repair this problem but I just don´t!! I have tried each possibility ever for 2 weeks daily and about 30 hours reading and trying! So this must be apple issues for sure!
I red yesterday that with the update to 10.10.1 there is a fix to the bug but still nothing!!
BY THE WAY!! this problem occurs to everyone using POP or IMAP mail... there are some people who solved this issue with some luck or with some remendations on this link: Re: Mail SMTP (outgoing) does not work after Yosemite upgrade
BUT; There are some other people like me that have try everything.. even formatting the computer, creating new mail accounts from the same server, from 3 different mac´s retina ,core 2 duo core i7 , etc )
yosemite is not what I was expecting for months!, it crashes and crashes and It is annoying.
best regards
carlos fonseca

I was having the same problem as everyone else regarding the upgrade to Yosemite and the smtp errors. I didn't see any questions regarding Outlook for Mac so I just decided to try some different things. What worked for me was using the Apple Mail Settings Lookup (google it). I discovered that the Server Port numbers that were entered into my account preferences and what were shown on the Mail Settings Lookup were different. If you find when you do this your Server Port numbers are different do the following: Open Preferences in Outlook, click Accounts. Then you will have to put a check in the Override Default Port for both the Incoming and Outgoing servers (if both of your Server Port numbers are different). After I did this, my outgoing mail sent with no problems. Hope this helps someone out there!

How to satisfy POP-before-SMTP outgoing authentication?

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