Step-by-step: fix “email sent as another user” using Google Workspace SMTP Relay + PostMaster – BisonKB

Step-by-step: fix “email sent as another user” using Google Workspace SMTP Relay + PostMaster

Posted on 01-11-2025 | Category: General | Views: 35


A) Google Workspace (Admin Console) — set up SMTP Relay

  1. Open: Admin Console → Apps → Google Workspace → GmailRoutingSMTP relay serviceAdd Setting.

  2. Description: PostMaster SMTP Relay.

  3. Allowed senders: Only addresses in my domains.

  4. Authentication:

    • Only accept mail from the specified IP addresses (add your PostMaster public outbound IP(s)).

    • Require SMTP Authentication (leave unchecked).

  5. Encryption: ✅ Require TLS encryption.

  6. Save.

Also check DNS & security (strongly recommended)

  • SPF (domain DNS TXT):

    v=spf1 include:_spf.google.com ~all

  • DKIM: Admin Console → Apps → Google Workspace → Gmail → Authenticate email → select domain → Generate new record, publish the TXT in DNS, then Start authentication.

  • DMARC (optional but recommended, domain DNS TXT):

    _dmarc.yourdomain.com TXT "v=DMARC1; p=quarantine; rua=mailto:dmarc@yourdomain.com; fo=1"

    (Adjust policy later to reject when you’re confident.)

Why IP-based relay (no per-user auth)?
Because your gateway (PostMaster) sends for many users. If you auth with one mailbox (e.g., dcf@…), Gmail rewrites the envelope sender to that user → replies go to the wrong inbox. IP-based relay preserves each user’s From/Return-Path properly.


B) PostMaster (Mail Server) — map fields to your UI

Mails → Outgoing → Primary

  • Enabled: ✅

  • SMTP Host: smtp-relay.gmail.com

  • Port: 587

  • SSL Enabled: set to Always (your UI uses this to permit TLS)

  • TLS Support: ✅ (check it; this forces STARTTLS on 587)

  • User Authentication: unchecked (relay is IP-based; no username/password)

  • Auth Type: leave at Plain (ignored since auth disabled)

  • Username / Password: blank

Outgoing Mail – Advance Settings (unchanged unless you need them):

  • Pause Mode Settings: leave default/off.

  • Connections: Max Clients (Relay) = 1–5 (start with 1).

  • Socket Timeout: 300 sec (defaults are fine).

SMTP Sender Masking

  • Enabled: ✅

  • Mode: All Mails

  • Email Address: leave blank (so each message uses each user’s own From).

Outgoing Mail – POP Before SMTP

  • Use POP Before SMTP: unchecked/disabled (not needed; you’re IP-authenticated at Google).

Save / Confirm changes.**


C) Outlook (end-user profiles)

For each user (e.g., abc@xyz.com):

  • Account type: Microsoft 365/Google via OAuth or standard IMAP/POP for incoming only.

  • Outgoing (SMTP) in Outlook should point to PostMaster, not directly to Gmail.

  • From address = the user’s own mailbox (abc@xyz.com).

  • Do not reuse dcf@xyz.com credentials anywhere.

  • Avoid “Send As” or “On behalf of” unless it’s intentional and permissioned.


D) Testing (prove it works)

  1. Send a mail from abc@xyz.com to an external mailbox (e.g., Gmail/Outlook.com).

  2. In the recipient mailbox, open Show original / View message source and verify:

    • From: abc@xyz.com

    • Return-Path: abc@xyz.com (or a Google bounce alias for the same user)

    • Authentication-Results: shows spf=pass and dkim=pass (after DKIM is live).

  3. Reply from the recipient — it should go back to abc@xyz.com, not dcf@xyz.com.

  4. In Google Admin → Reports → Email Log Search, confirm messages are accepted via SMTP relay from your PostMaster IP.


E) Common pitfalls & quick fixes

  • Still shows dcf@… as sender
    → You’re still using smtp.gmail.com with auth somewhere. Change to smtp-relay.gmail.com:587 and disable auth on PostMaster.

  • Relay rejected
    → Wrong/changed public IP. Verify the egress IP of PostMaster and add it to the allow list in the SMTP relay setting.

  • No TLS
    → Port/checkbox mismatch. Use 587 + STARTTLS (TLS Support checked).

  • SPF softfail
    → SPF record missing _spf.google.com.

  • Some devices can’t do TLS/auth (legacy scanners, etc.)
    → Keep the same relay but add their source IPs to the allowed list. Use port 587 with STARTTLS if possible; if truly incapable, consider a dedicated smart host inside your LAN that can up-convert to TLS.


Full Article (Shareable Guide)

Subject

Stop Sender Mix-ups in Google Workspace: A Complete PostMaster + SMTP Relay Setup to Ensure Replies Reach the Right Inbox

Overview

Organizations that run a local mail gateway (like PostMaster) and Google Workspace often see a subtle but damaging issue: users send as abc@yourdomain.com, but recipients receive mail as dcf@yourdomain.com. Replies route to the wrong person, conversations split, and customers get confused.

This happens when your gateway authenticates to Gmail with one user’s mailbox (dcf@…) and sends mail for many users. Gmail correctly rewrites the envelope sender to the authenticated account — so replies follow that identity.

The fix is to use Google Workspace SMTP Relay with IP-based authentication and to configure your gateway to preserve each user’s From address (SMTP Sender Masking). This guide shows every screen and value you need.


1) Prerequisites

  • Google Workspace Super Admin access.

  • Your PostMaster server’s public outbound IP.

  • Ability to edit your domain’s DNS (TXT records for SPF/DKIM/DMARC).


2) Configure Google Workspace SMTP Relay

  1. Admin Console → Apps → Google Workspace → Gmail → RoutingSMTP relay serviceAdd setting.

  2. Description: PostMaster SMTP Relay.

  3. Allowed senders: Only addresses in my domains.

  4. Authentication:

    • Only accept mail from the specified IP addresses → add your PostMaster public IP.

    • ☐ Leave Require SMTP Authentication unchecked.

  5. Encryption: ✅ Require TLS encryption.

  6. Save and note the server name you’ll use: smtp-relay.gmail.com.

SPF, DKIM, DMARC (deliverability & trust)

  • SPF: v=spf1 include:_spf.google.com ~all

  • DKIM: enable per domain in Admin Console and publish DNS TXT; then Start authentication.

  • DMARC: start with p=quarantine, move to p=reject later.


3) Configure PostMaster (SMTP Smart Host)

Outgoing → Primary

  • Enabled: ✅

  • SMTP Host: smtp-relay.gmail.com

  • Port: 587

  • SSL Enabled: Always

  • TLS Support: ✅

  • User Authentication: unchecked

  • Auth Type: Plain (ignored when auth off)

  • Username / Password: blank

SMTP Sender Masking

  • Enabled: ✅

  • Mode: All Mails

  • Email Address: blank (so each message uses the sender’s address)

POP Before SMTP

  • Disabled

Connection limits/timeouts: defaults are fine; increase Max Clients if throughput is low.

Rationale: With IP-based relay and no per-user authentication, Gmail accepts mail from your gateway on behalf of any @yourdomain.com mailbox — and it will not rewrite the sender identity. Sender Masking ensures the From and envelope sender carry the correct user.


4) Outlook Profile Guidance

  • Each user’s account identity must be their own (abc@yourdomain.com).

  • SMTP in Outlook should aim at PostMaster (which then relays to Google), not smtp.gmail.com.

  • Do not reuse shared credentials (dcf@…) anywhere.

  • Only use “Send As / Send on behalf” when officially granted — and expect replies to follow that identity.


5) Validation & Troubleshooting Workflow

  1. Send test from abc@yourdomain.com to external mailbox.

  2. Inspect headers at the recipient:

    • From: = abc@yourdomain.com

    • Return-Path: = abc@yourdomain.com (or Google alias for the same)

    • Received: shows smtp-relay.gmail.com with TLS.

    • Authentication-Results: shows spf=pass (after DNS TTL) and dkim=pass (after DKIM live).

  3. Reply from recipient and confirm it lands in abc@yourdomain.com.

  4. If rejected:

    • Verify the public IP in the relay allow list matches the actual egress IP.

    • Ensure TLS is on (587 + STARTTLS).

    • Confirm Allowed senders is set to Only addresses in my domains.

    • Check Google Admin → Email Log Search for the exact error.


6) Security & Policy Tips

  • Restrict the relay to only your IPs; never open relay to the world.

  • Enforce Require TLS (already enabled).

  • Rotate/monitor gateway IPs (if you change ISP/NAT, update the relay setting).

  • Implement DMARC reports (RUA) to monitor spoofing attempts.

  • Keep PostMaster patched; limit concurrent connections if you see throttling.


7) FAQ

Q: Can I keep using smtp.gmail.com with app passwords?
A: Not for a multi-user gateway. That method binds all traffic to the authenticated mailbox and causes the identity mix-up you observed.

Q: Can scanners/copiers use this relay?
A: Yes — add their source IPs to the same SMTP Relay and send via smtp-relay.gmail.com:587 with STARTTLS (no auth).

Q: We host multiple domains.
A: Add each verified domain in Workspace; keep Allowed senders: Only addresses in my domains. Ensure SPF/DKIM/DMARC for each domain.

Q: We still see occasional replies going to the wrong user.
A: Check if anyone is using an old profile that still points to smtp.gmail.com with dcf@… credentials; migrate them to the gateway profile.


8) Final Checklist (1-minute audit)

  • Google SMTP Relay exists with Allowed senders = Only addresses in my domains

  • Only accept mail from specified IPs = your PostMaster public IP(s)

  • Require TLS checked

  • PostMaster uses smtp-relay.gmail.com:587, TLS on, no auth

  • SMTP Sender Masking = Enabled (All Mails)

  • SPF includes _spf.google.com; DKIM enabled; DMARC set

  • Outlook sends to PostMaster; no shared mailbox credentials anywhere


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Tags:
Google Workspace Gmail SMTP relay smtp-relay.gmail.com PostMaster mail gateway smart host STARTTLS TLS port 587 port 465 Outlook app password envelope sender Return-Path From header Reply-To sender masking SMTP sender masking IP allowli
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