I reach to make it works some weeks ago, but it doesn’t anymore (I don’t remember to have change my settings). Here they are :
WM_SocketSMTP.Address = “smtp.free.fr”
WM_SocketSMTP.Port = 587
WM_SocketSMTP.SSLConnectionType = SSLSocket.SSLConnectionTypes.SSLv23
WM_SocketSMTP.SMTPConnectionMode = 1
WM_SocketSMTP.SSLEnabled = True
WM_SocketSMTP.Username = “tom.25” ’ my email is @free.fr
WM_SocketSMTP.Password = “MyPassword”
In this case, the email never go, the program wait and wait until I cancel.
If I do :
WM_SocketSMTP.SSLEnabled = False
Then the email seems to have been sent but no.
As if I do :
WM_SocketSMTP.Port = 465
It seems to have been sent but neither, no. 
My settings are the same as in Apple Mail (where I can send email) except authentification which is (if I translate in English) “Answer to chalenge MD5”
Note I hesitate to write inFrench and post in the French sub-forum. But maybe I do something wrong. I have an Address Orange and it works, except the port is 465.
as tu activé l’envoi de mail sécurisé sur le portail de ton compte free ?
as tu essayé d’envoyer un mail sans aucun mot de passe ni identifiant
(si tu envoie depuis une freebox il n’y a pas besoin d’identifiant ni de mot de passe)
You should get at least an error or a timeout. The part where you make your email is missing from the code.
Try with the CURL plugin from MBS or the Chilkat plugin. The plugins have much better error reporting.
Merci jean-Yves, oui c’est bien activé. j’ai sur ma page Free :
Votre login "tom.25" est déjà autorisé à faire du SMTP authentifié sur "smtp.free.fr".
Seules les méthodes d'authentification avec mot de passe chiffré sont acceptées. Par exemple l'utilisation du SSL (sur le port 465) ou du 'MD5 Challenge-Response' (sur le port 587).
Pour désactiver cette fonctionnalité, cliquez ici:
Si j’essaye sans identifiant, mon programme (Xojo) me retourne immédiatement l’erreur :
Server Error 554554 5.7.1 <unknown[109.221.31.99]:53928>: Client host rejected: Access denied
Je suis chez Sosh (Orange), j’ai une LiveBox et non une Freebox.
HS : Et avant hier ils ont posé la fibre devant chez moi. Ca arrive 
Thanks Beatrix, no Xojo doesn’t display any error. This morning I received one of the emails I sent me yesterday during my test, but which settings it was ???
I prefer to stay with Xojo code, I know MBS pluggins are wonderfull but I can’t buy them. And learn to use another pluggin is too long for me. I will send my email with another host (orange) if I can’t with Free host.
Beatrix, I didn’t paste all my code but it works when I use other host.
I just see that the instruction :
WM_SocketSMTP.SMTPConnectionMode = 1
is API1 and is not shown as deprecated. It should be :
WM_SocketSMTP.SMTPConnectionType = SMTPSecureSocket.SMTPConnectionTypes.SSLTLS
I will fill a FeedBack. (it does not resolve my problem).
I didn’t paste all my code but it works when I use other host.
It works with another host ?
Usually, you can only use the SMTP server from your current provider, i.e. you can use smtp.free only if you are currently connected to the internet via a Free account. If you, let’s say your phone, is connected to another network like Orange or SFR, then the server smtp.free will reject your connection.