I can't send emails with my Apple Mail client

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Any ideas? Using Apple Mail (now v 7.3), for at least a year I have been unable to SEND e-mails from my IMH website account. I can get e-mails fine, and can send via 4 other accounts via other hosting & gmail, but not this one on IMH. Two different Customer Service people have helped a lot today, getting the settings right and trying different things, including deleting the mail accounts and servers and setting them up from scratch. We have tried both the normal server name and the actual server number. The error remains "Cannot send message using the server... The connection to host vpsXXXX.inmotionhosting.com on port 465 failed."
SSL is checked. But we also tried the non-SSL switch with corresponding port, and I'm not positive if it was with the identical results, but it didn't work. Multiple Mail restarts, and an OS restart, without change. Deleted test messages in the Outbox and wrote new ones, no change. I have always gotten the warning about the certificate when connecting, and today I found the settings to "always trust" so that I don't get that message and have to select to connect - had to put in my MacBook Pro password to allow the change. After restarting Apple Mail the certificate message was gone, but I still have the same failed connection to the outgoing mail server.
Customer Service suggested the Community Support, since there seems to be no reason why it will not connect. I absolutely hate using webmail because I have too many accounts to manage - if they don't come into my group Apple Mail mailbox, they just don't get checked. Any ideas how to resolve this?
Hello Ultimate7, Sorry for the problems with your Apple Mail client. I actually am a long time MacBook Pro user myself, though I've typically avoided the Apple Mail client for managing mail. I went and re-tested this issue on my own VPS and in the process I created a video about it. The video is titled "Setting Up the Apple Mail Client with a VPS", but I verify that the outgoing mail works in the process. I use the VPS settings and show you how to stop those certificate warnings as well. If you require more info on a summary of the email settings, please see How to find your email settings. Also, please make sure to review the article dealing with problems sending email. The video was just finished, so it's possible that YouTube is still processing it, but hopefully, it should help resolve your problem. The main difference is that I'm using the latest version of Yosemite on my MacbookPro with the Apple Mail client version 8.2. I have no access to the earlier version. The setup is basically the same, though. If you continue to have problems then we can double-check here by setting up an email directly with your VPS. Beyond that, it would be suggested that you talk with Apple support. If you do continue to have problems after reviewing the video, then please let us know so that we can investigate the issue in more depth. Kindest regards, Arnel C.