Please provide much more information, such as your account, your account setup for incoming and outgoing and the error message. Thank you.

Im not having the issue sending it through outlook, i could not send through thunderbird were i send my estimates through, other issue is that it keeps wanting me to reset password and it's trying to send it through my landline. We did straighten it out where its sending us the passwords to other email but again we still cant send emails emai- Hilltopbodyshop@outlook.com

Maybe if you post some specifics: the account inbound settings and the SMTP server settings (server name, port number, authentication, connection security) that may help a lot. Outlook isn't my strength, but if the info is posted, someone here may have suggestions. Thank you.

my experience. Version 115.5.2 32-bit. Won't send sticks at sending then says "Sending of the message failed. The message could not be sent because the connection to Outgoing server (SMTP) smtp.office365.com timed out. Try again".

see screenshot. If I go into hotmail and send it will download into my sent items

my settings

Ok, I'm not well-versed with office365, but you mentioned your email is at @outlook.com, but your SMTP server is set to a hotmail account. If your email is at @outlook, that may be the error. Try setting the SMTP server to that address.

Ok, I'm not well-versed with office365, but you mentioned your email is at @outlook.com, but your SMTP server is set to a hotmail account. If your email is at @outlook, that may be the error. Try setting the SMTP server to that address.

not sure is that for me? It has been working at those settings for ages. isn't outlook and hotmail now the same. ? and chaneged to auth02 for security

Well, the two email addresses are different accounts. Did you try making the change?

Well, the two email addresses are different accounts. Did you try making the change?

yes it didnt work. Has been like that ages and worked

Email providers have been making security changes this year and they are often not well communicated to their users. It seems you have a hotmail account and an outlook account? It may help if you post a screenshot of the input server settings for the outlook account. Is the hotmail account also a problem?

fixed smtp outgoing server somehow got changed

Is it now working?

yes it is

Good to know. Thank you.

stopped working again going to get a real email program. This is a crock of shit