# Email from Lightroom on Mac



## magician john (Dec 3, 2019)

I have started to get an error message when trying to Email a photo out of Lightroom Classic on my mac.

"failed to establish connection with outgoing mail server"

I have not altered any settings so please advise what is happening and what I can do.

I have even got this message when trying to send to my own email id.


----------



## clee01l (Dec 3, 2019)

Your mail Server has probably implemented a two factor authentication and your mail client (in this case Lightroom) needs to be authenticated with a special password.   Check with your mail server host to determine the process they require.


----------



## magician john (Dec 3, 2019)

i am still able to send mails outside of Lightroom, so would this still be the case?


----------



## clee01l (Dec 3, 2019)

Lightroom is the mail client  here and  your use another  mail client outside of Lightroom that has already been qualified for two factor  authentication.   Check with your mail service provider to see if they use two factor authentication and what steps you need to do to authenticate the Lightroom Mail client.


----------



## magician john (Dec 3, 2019)

I have rebooted my Computer, Updated LR.

I have spoken to Sky who confirm that i do not have two step verification set up, so it is not this that is causing the issue.
They cannot see any issues., especially as I can sent emails through Sky/Yahoo without any issue.
spent the whole afternoon on the telephone to Adobe and they so far have been unable to sort it. cannot get any account verified within the LR Email A/c Manager. This includes themselves setting up an account for them, outside of sky and still cannot get their Account Validated.
further ideas please.


----------



## Victoria Bampton (Dec 20, 2019)

Grab us a screenshot of the settings you're using John? If I remember rightly, Sky uses the Gmail interface, and Gmail have been messing with security recently.


----------



## magician john (Dec 20, 2019)

sky uses Yahoo.
let me know which settings you are after and I will  gladly send over. is it the "Email Account Manager"?
Adobe have had the issue since 3 December and still haven't fathomed out what to do about it.
believe there is a special way of attaching shots so please clarify for me.


----------



## clee01l (Dec 20, 2019)

magician john said:


> sky uses Yahoo.
> let me know which settings you are after and I will gladly send over. is it the "Email Account Manager"?
> Adobe have had the issue since 3 December and still haven't fathomed out what to do about it.
> believe there is a special way of attaching shots so please clarify for me.



Yahoo now uses two factor authentication You should have received some notice from Sky of this impending change. And what to do about it. 

This link applies to Gmail but should address Yahoo as well:

https://helpx.adobe.com/lightroom-classic/kb/issue-validating-email-account-lightroom.html
Sent from my iPad using Tapatalk


----------



## magician john (Dec 21, 2019)

I use my Sky/Yahoo mail quite successfully without any 2 step verification. It is only when I try to send photo emails from LR that this occurs.

Adobe even changed the settings so that you don't need a password at all in the Email account Manager, and still this still happens.

In the Email Account Manager, it is showing as "not validated" and that is before I try to send  an email.


----------



## clee01l (Dec 21, 2019)

magician john said:


> I use my Sky/Yahoo mail quite successfully without any 2 step verification. It is only when I try to send photo emails from LR that this occurs.


What mail client are you using?  The one accessed by the web browser already is two factor authenticated.   If you go through Outlook or AppleMail or any other third party mail app, it will still need to have two factor authentication invokes at least the first time.


----------



## magician john (Dec 21, 2019)

I use Sky/Yahoo.

I have avoided using Applemail to send emails as had big issues last year and most times it would not send the mail. It was easier to send via yahoo.
As it happens I have sent an email from LR via AppleMail and it went ok this time. No 2 step verification. I don't understand what you are saying.


----------



## clee01l (Dec 21, 2019)

magician john said:


> I use Sky/Yahoo.
> 
> I have avoided using Applemail to send emails as had big issues last year and most times it would not send the mail. It was easier to send via yahoo.
> As it happens I have sent an email from LR via AppleMail and it went ok this time. No 2 step verification. I don't understand what you are saying.


It is Two Factor authentication not Two Step authentication.
Here is a link for the mail client that I use (Airmail) describing the procedure for Yahoo
https://help.airmailapp.com/en-us/article/two-stepfactor-authentication-airmail-for-macos-ofnqg7/It is possible that you did this for AppleMail at one time.    Mail Clients need to interact with the mail server and if the server has implemented two factor authentication security then supplying a single unauthenticated password in the mail client is no longer sufficient.    Outlook, Apple Mail, Airmail, Eudora AND Lightroom are all mail clients


----------



## magician john (Dec 21, 2019)

I have checked with Sky and a two factor authentication has never  been set up.


----------



## clee01l (Dec 21, 2019)

magician john said:


> I have checked with Sky and a two factor authentication has never been set up.



I use AT&T which uses Yahoo. Yahoo implemented 2 factor authentication this year and i hat to update my AT&T passwords with authenticated ones. AT&T notified me of this well in advance, but I still had some accounts on some apps on some devices that stopped working when it became required at Yahoo.


Sent from my iPad using Tapatalk


----------



## magician john (Dec 22, 2019)

As a matter of interest whilst I am still looking at this, do you now have to get this second factor of authorisation, approved every time you go into LR or seeing a photo from LR?
I only use my mobile when out and only just in case needed so it is never on indoors. I wouldn't want to have to go through the process of using it indoors just to get into LR or sending a photo in LR or every time I go into my mail.


----------



## clee01l (Dec 22, 2019)

magician john said:


> As a matter of interest whilst I am still looking at this, do you now have to get this second factor of authorisation, approved every time you go into LR or seeing a photo from LR?
> I only use my mobile when out and only just in case needed so it is never on indoors. I wouldn't want to have to go through the process of using it indoors just to get into LR or sending a photo in LR or every time I go into my mail.



The way it works is by app. For example the iCloud mail server requires two factor authentication. You go to some website associated with the server and authenticate your password one time. That site generates an app specific password that looks nothing like your real password. You put that generated password into the mail client app password field and every time your mail client sends that app specific password to the server, the server recognizes it as valid and authorized. 

This is what Two factor authentication means. Two step authentication actually involves two steps. In the first step you send your password to the mail server. In the second step in the mail server send you usually via text message and authenticated code. You send this second step code to the mail server and it then knows that you are you and that your mail request is valid. Two step authentication has to be done every time you request mail. To factor authentication is done ahead of time with a password generated by the server to be recognized by the server as associated with your email account.


Sent from my iPad using Tapatalk


----------



## magician john (Dec 22, 2019)

clee01l said:


> The way it works is by app. For example the iCloud mail server requires two factor authentication. You go to some website associated with the server and authenticate your password one time. That site generates an app specific password that looks nothing like your real password. You put that generated password into the mail client app password field and every time your mail client sends that app specific password to the server, the server recognizes it as valid and authorized.
> 
> This is what Two factor authentication means. Two step authentication actually involves two steps. In the first step you send your password to the mail server. In the second step in the mail server send you usually via text message and authenticated code. You send this second step code to the mail server and it then knows that you are you and that your mail request is valid. Two step authentication has to be done every time you request mail. To factor authentication is done ahead of time with a password generated by the server to be recognized by the server as associated with your email account.
> 
> ...


Thank you.
so  what happens for people who do not have a mobile phone?


----------



## clee01l (Dec 22, 2019)

magician john said:


> Thank you.
> so  what happens for people who do not have a mobile phone?


Usually the authentication site assumes that you can receive text message. Email is an alternative but not instantaneous like a text.   And there might be an option for a POT call from a live or automated  source connected to the server.


----------

