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Avoid Checkpoint Rerouting emails - Exchange Transport Rule
Step-by-step: Metacompliance Bypass Checkpoint transport rule
1. Navigate to the rule
Go to Exchange Admin Center → Mail flow → Rules (or Microsoft Defender portal → Email & collaboration → Policies & rules → Mail flow → Rules).
2. Create the rule
Name it: Metacompliance Bypass Checkpoint
3. Set the condition
- Apply this rule if: The sender → IP address is in any of these ranges or exactly matches
- Enter your Metacompliance sending IP range(s), shown here.
4. Set the actions (add both, in this order)
- Action 1: Modify the message properties → set a message header
- Header name:
X-CLOUD-SEC-AV-Info - Header value:
enteryourcheckpointappnamehere,office365_emails,inline - Action 2 (add via the +): Stop processing more rules
This second action is the critical piece that was missing — without it, Exchange keeps evaluating lower-priority rules (like Check Point - Protect) even after this one fires, which is why mail was still routing to Check Point.
5. Except if
Leave blank unless you need to exclude specific senders/recipients from the bypass.
6. Set rule priority (Settings tab, or the rule list after saving)
- This rule's priority number must be lower than the Check Point - Protect rule's priority number (in Exchange, priority 0 runs first, then 1, 2, 3...).
- Go to Mail flow → Rules, and drag this rule (or set its Priority value) so it sits above Check Point - Protect in the list.
- Confirm by checking each rule's Priority field: e.g., if Check Point - Protect is currently priority 2, set this rule to priority 0 or 1 — anything numerically lower.
7. Save and test
- Save the rule.
- Send a test message from an IP in the allowed range.
- Run a Message Trace and confirm:
Metacompliance Bypass CheckpointfiresCheck Point - Protectdoes not appear in the trace afterward