SMTP-send-only is no longer working in Outlook.com

Hi, thanks for your reply but I'm not trying to send SMTP through Outlook, I'm trying to send SMTP through my web hosting provider (Hostmonster). 

I know the settings I have to send only with SMTP work in Gmail, but they no longer work in Outlook.com.

Any ideas?

To set up SMTP-send-only:

1. I go to Settings|Mail|Sync Email
2. I click on "Other email accounts"
3. I enter Display Name, Email Address, and Password for the email account I'm trying to sync on Hostmonster
4. I select "Import into existing folders..."
5. I select "Manually configure account settings..."
6. On the next screen I select "SMTP send-only connection settings"
7. For Outgoing SMTP server I enter host423.hostmonster.com
8. For Outgoing Server Port I enter 465.
9. I click OK

I know these settings are correct because I have an SMTP-send-only account set up in Gmail for this same account with these settings and it works fine.

When I send an email with my synced account (which is also my primary alias) in Outlook.com, it never sends. It just sits in the Drafts box.

The only errors I get are "Something went wrong and we haven't sent your message yet." and "This message hasn't been sent." 

I can send from my Outlook email address fine. It's just my SMTP-send-only account that doesn't work.

Please Note: This USED TO WORK until about three days ago. Then it stopped working on all Outlook.com platforms (all browsers and the iPhone app). I hadn't made any changes on my end to cause this.

Thank you for any help!

Me too me too me too me too! The exact same issue as MarcMenninger's, & I also noticed it yesterday (3/22/19), so whatever change could be causing it, it must have happened in the last couple of days. It is really annoying, as it has been working for years without a glitch, and now all of a sudden, without any warning, it just stopped working.

To give even more details; as OP described, the sent mails are just sitting in the Drafts folder with the very obscure "Something went wrong..." message near the top. Then, if I open one of these mails for editing & try to send it again, a small error window pops up, and when clicking on "More information", it gives a little more helpful error message: "You don't have permission to perform this action." Now we are talking! So it seems that whatever the outgoing server is (probably not the original send-only SMTP server, but an Outlook server), it refuses to recognize the send-only account's email address (an email alias for Outlook.com) as a legit sender.

Microsoft team, please try to fix this issue quickly. I've been quite happy with Outlook.com, & would hate to say good-bye to it. Thanks!

***** FOUND A WORKAROUND! *****

Short answer: I used modified POP3 settings instead of SMTP-send-only.

The reason why I didn't use POP3 settings in the first place is because Outlook.com has a flaw where it doesn't apply Rules to emails coming from POP3 accounts. This is a major problem for me since I apply A LOT of rules to keep my emails organized.

But there's a way to set up POP3 to act like SMTP-send-only and not have to deal with emails that don't obey Rules. I was inspired by the response starting with "You don't really need to have a domain..." here:

https://answers.microsoft.com/en-us/outlook_com/forum/oemail-osend/remove-outlookcom-on-behalf-of-when-sending-from/c5339e0e-07b2-4ce6-846b-7c631262c30d

Basically:

• You need to create a "dummy" extra email account with your ISP or hosting company. This account will almost never get emails so you don't have to worry about a bunch of emails that can't be managed with Rules.
• Next, you fill out the POP3 settings for your synced account to use both your dummy account and target account info. I explain the settings below.
• Then you need to forward the emails from your target account at your ISP to your Outlook email address. Rules will work for these emails.

Here's how I did the settings in Outlook.com:

1. Go to Settings|Mail|Sync Email
2. Click on "Other email accounts"
3. Enter Display Name (what you want people to see as your name), Email Address (the address of the account you're trying to sync on your ISP), and Password (this is the password for your dummy account)
4. Select "Import into existing folders..." (if you want)
5. Select "Manually configure account settings..."
6. On the next screen be sure to enter the username for your dummy account in the "User name" field toward the top. The password for your dummy account you entered earlier should carry over here.
7. Select "POP/SMTP connection settings"
8. For "Incoming (POP) server" enter the settings specified by your ISP
9. For "Outgoing SMTP server" enter the settings specified by your ISP
10. Leave the rest of the settings as is
11. Click OK

Please try this and let me know if it works for you.

change 8. For Outgoing Server Port I enter 465. on 8. For Outgoing Server Port I enter 587.

check and write result