Email System Setup in Total Office Manager (Outbound SMTP)

This is a supplemental help topic to help users understand the email setting found in Preferences > Company > My Preferences > Use Alternative SMTP Email.

What you’ll need from your Email Provider / IT

Ask for:

• Outgoing Mail (SMTP) server name (SMTP host)
• Port
• Encryption method (what your provider expects on that port)
• E-mail Username (almost always your full email address)
• Password
  • If MFA / 2‑step verification is enabled, you may need an App Password / app-specific password (common for Gmail, Yahoo, iCloud, Zoho).

Where to Enter the Settings (field-by-field)

Open TOM’s email settings screen and use these exact fields:

1. Use Alternative SMTP Email ✅
   Turn this on to use the SMTP settings below.
2. E-mail Username
   Usually your full email address (example: you@yourcompany.com).
   This is also what TOM uses to authenticate if you enter a password.
3. Password
   Your email password or an app password if required by your provider.
4. Mail From Name
   The friendly name recipients will see (example: James Leichter).
5. Mail From Email
   The “From” address recipients will see (example: you@yourcompany.com).
   Best practice is to make this match the mailbox you authenticate with, unless your provider/IT has explicitly configured “Send As” permissions. Microsoft 365 calls this out as a common cause of send failures if the authenticated mailbox doesn’t have permission to send as the From address.
6. Bcc (optional)
   If filled in, every message will Bcc that address.
7. Outgoing Mail (SMTP)
   Your provider’s SMTP host (example shown in your screenshot: smtp.office365.com). Microsoft’s documented SMTP submission host is smtp.office365.com.
8. Port
   Usually 587 (recommended) or 465 (depending on provider).
9. Encryption (dropdown)
   Pick the encryption that matches the port/provider:
   • STARTTLS → typically 587 (recommended submission port)
   • SSL/TLS → typically 465 (implicit TLS)
   • Auto → recommended when you’re not sure (let’s TOM choose the appropriate secure connection style)
   • None → only for special cases like a trusted internal relay
10. This is a Microsoft Exchange Server
    Leave this unchecked for normal SMTP (including Microsoft 365/Office 365 SMTP). Only check this if Aptora support or your IT explicitly tells you to use an Exchange/EWS-style configuration instead of SMTP.
11. Click Test Account Settings
    This tests the settings you entered. (A successful test confirms TOM could connect and send; it doesn’t guarantee final delivery/read—always check spam/junk and any provider-side quarantine.)

Recommended Port/Encryption Combinations

• 587 + STARTTLS is the most common “authenticated submission” setup (best default).
• 465 + SSL/TLS is a common secure alternative when a provider specifically requires implicit TLS.

Email Provider Examples:

Microsoft 365 / Office 365 (Exchange Online)

Outgoing Mail (SMTP): smtp.office365.com
Port: 587 (recommended) (25 is also used in some scenarios)
Encryption: STARTTLS
E-mail Username / Password: the mailbox sign-in credentials

Important note for support cases: Microsoft 365 tenants often have SMTP AUTH disabled globally (security defaults) or per mailbox. If authentication fails, the admin may need to enable “Authenticated SMTP” for that mailbox.

Google (Gmail / Google Workspace)

Outgoing Mail (SMTP): smtp.gmail.com
Port/Encryption: 587 + STARTTLS or 465 + SSL/TLS
If login fails and MFA is enabled, you may need an App Password (Google requires 2‑Step Verification to create one).

Yahoo Mail

Outgoing Mail (SMTP): smtp.mail.yahoo.com
Port: 465 or 587
Yahoo requires authentication and typically requires generating an App Password.

Apple iCloud Mail

Outgoing Mail (SMTP): smtp.mail.me.com
Port: 587
Apple lists SSL as required; if SSL errors occur, try TLS/STARTTLS. Apple also specifies app-specific passwords.

Zoho Mail

• Free/personal accounts: smtp.zoho.com
• Paid org/custom domain accounts: smtppro.zoho.com
  Ports: 465 (SSL) or 587 (TLS) and authentication required.

Quick Troubleshooting Checklist (most common failures)

• Correct port + matching encryption (587=STARTTLS, 465=SSL/TLS).
• If webmail login works but SMTP fails: you likely need an App Password (Gmail/Yahoo/iCloud/Zoho).
• Microsoft 365: confirm SMTP AUTH is enabled for that mailbox.
• If messages are rejected: ensure Mail From Email is allowed for the authenticated account (“Send As” permissions if different).