mails are not being sent
In 9 cases out of 10, one of the SMTP values is wrong. Work through these steps.
🔎 1. Find the real error
The error is in the AwareIM Server output, not in the rule log. Look for lines like these:
Email was not sent due to exception javax.mail.MessagingException ...
Emails that failed are saved in AwareIM/UNSENT_EMAIL/<business space>. AwareIM tries to send them again every 10 minutes.
⚙️ 2. Check the SMTP settings
Double-click the business space version, then open Outgoing Emails.
- Note whether the values come from SystemSettings or from the Configuration Tool. If they come from SystemSettings, check the values in the SystemSettings record at runtime.
- Check whether a business object has its own email channel. Look on its Intelligence tab for “Use values below”. That channel overrides the global settings.
- A
SEND … USING OutgoingEmailAccount also overrides the global settings.
🔌 3. Port and SSL/TLS must match
| Port | Tick | Untick |
|---|
| 587 (most providers, Office 365, Gmail) | TLS | SSL |
| 465 | SSL | TLS |
| 25 | Neither, unless your provider says otherwise | |
Do not tick both boxes. AwareIM uses STARTTLS when TLS is ticked.
👤 4. Login and “From” address
| Error | Fix |
|---|
AuthenticationFailedException | Check the user name and password |
No authentication mechanisms supported by both server and client | Tick TLS |
The From address must be a mailbox your mail server knows. Many servers reject a From address they do not host.
Gmail and other providers with two-factor login need an app password. Your normal password does not work.
☁️ 5. Office 365 / Microsoft 365
Microsoft blocks basic SMTP login for many tenants. You see Authentication unsuccessful … security defaults policy when this happens.
✅ Fix (pick one):
- Ask your Microsoft 365 admin to enable SMTP AUTH for the sending mailbox.
- Use Emails will be sent using Microsoft Graph in the Outgoing Emails dialog. You need a client ID, secret and tenant ID from Microsoft. This option is only in recent builds.
🔐 6. Certificate and TLS errors
| Error | Cause | Fix |
|---|
Could not convert socket to TLS, SSLHandshakeException, PKIX path building failed | Java does not trust the mail server’s certificate | Import the mail server’s root certificate into the AwareIM Java: see step 2 of the SSL reply |
Could not convert socket to TLS that comes and goes, or a warning that TLS 1.0 is ending | Older AwareIM builds ship an old mail library and an old Java | Upgrade to a current build. Do not copy in mail.jar files by hand |
🌐 7. Can the server reach the mail host?
| Error | Fix |
|---|
Could not connect to SMTP host, Connection timed out, UnknownHostException | Test the host and port from the AwareIM server, for example telnet smtp.office365.com 587 or Test-NetConnection smtp.office365.com -Port 587. If this fails, a firewall, the hosting company or a wrong host name is the cause |
Many cloud hosts block port 25. Use 587 instead.
✉️ 8. The rule itself
SEND MyEmail TO Customer needs Customer to be an intelligent object with an Email channel.- To send to a plain address, use a rule like this:
CREATE MyEmail WITH MyEmail.BCC = 'someone@example.com'SEND MyEmail
No Recipient Address means the recipient attribute was empty.Missing '<' means the From address has a bad format. Use Name[addr@example.com](mailto:addr@example.com).
🧪 Quick test
Make SystemSettings intelligent, with an Email channel pointing at your own address. Then run a one-line process:
SEND OutgoingEmail_Test TO SystemSettings
Still stuck? Post the exact exception from the server output, your provider, the port, and which boxes are ticked.
