Email security troubleshooting and support for complex environments.
Fast, expert troubleshooting and ongoing support for email delivery, security policies, integrations and mail-flow issues across Proofpoint, Microsoft 365, Cisco and multi-vendor environments.
Expert support across your email ecosystem
Troubleshoot, resolve and optimize issues across the supported technologies in your environment.
- End-to-end mail-flow troubleshooting
- Multi-vendor integration and policy support
- Evidence-led analysis and practical resolution guidance
Common issues we help you resolve
We investigate, isolate and resolve a wide range of email security and mail-flow issues across supported environments.
Mail delivery failures
Investigate non-delivery, delays, unexpected bounces and recipient-specific delivery problems across internal and external mail flow.
Proofpoint and Microsoft 365 integration issues
Troubleshoot issues between Proofpoint and Exchange Online, including connectors, policies, routing and message flow.
SMTP, TLS and certificate errors
Troubleshoot SMTP connectivity, TLS negotiation failures, certificate validation and secure-delivery problems.
Authentication and deliverability problems
Investigate SPF, DKIM, DMARC and sender-reputation issues affecting authentication, policy enforcement and email delivery.
Connector and routing issues
Diagnose connector misconfiguration, mail-flow rules, routing paths and dependencies across supported platforms.
Intermittent and hard-to-reproduce issues
Perform evidence-led analysis of time-specific, recipient-specific or environment-specific failures that are difficult to reproduce consistently.
False positives and policy behavior
Identify why legitimate messages are being blocked or quarantined, investigate policy conflicts and apply targeted tuning while maintaining appropriate security controls.
Ongoing operational support
Provide specialist assistance with operational issues, configuration changes, policy updates and recurring email security requirements where ongoing support forms part of the engagement.
Troubleshooting process
A structured approach to quickly identify, resolve and validate email security issues.
Understand
Capture symptoms, impact, affected systems, timeframe and business context.
Gather evidence
Collect relevant logs, message trace data, SMTP responses, headers and configuration evidence.
Isolate
Analyze the evidence to identify the system, policy, route or control responsible for the issue.
Remediate
Implement the agreed configuration, policy or routing change required to address the root cause.
Validate
Confirm expected behavior and test end-to-end mail flow after remediation.
Document
Provide findings, actions taken, validation results and recommendations where appropriate.
Example: Mail delivery failure
An illustrative example showing how we investigate and resolve an email delivery issue.
- Environment
- Proofpoint → Microsoft 365 (Exchange Online)
- Symptom
- External messages to a specific recipient scope are rejected
- Observed
- Message accepted by SMTP, then failed during downstream transport-policy processing
- Investigation
- Reviewed SMTP response, message trace, gateway logs, connector configuration and mail-flow policy scope
- Finding
- A recipient-scoped mail-flow rule was incorrectly rejecting the affected messages
- Resolution
- Corrected the affected policy scope, validated end-to-end mail flow and confirmed successful delivery
220 mx.example.mail.protection.outlook.com Microsoft ESMTP MAIL Service ready
EHLO relay.security.example
250-SIZE 157286400
250-STARTTLS
250-PIPELINING
MAIL FROM:<sender@example.net>
250 2.1.0 Sender OK
RCPT TO:<user@example.com>
550 5.7.1 Message rejected by organization policyRecipient: user@example.com Direction: Inbound Status: Failed Stage: Recipient evaluation Detail: Message rejected by organization policy Correlation: affected recipient scope only
Gateway action: Message accepted for delivery Next hop: Exchange Online TLS: Negotiated successfully Post-acceptance failure: 550 5.7.1 organization policy rejection Observation: transport reached Microsoft 365 successfully
Source: Proofpoint secure email gateway Destination: Microsoft 365 Connector state: Enabled TLS state: Successful Routing: Expected path confirmed Policy review: recipient-scoped rule evaluated
Finding: recipient-scoped mail-flow rule rejected legitimate mail Action: affected rule scope corrected Validation: external test messages delivered to affected recipients Result: expected end-to-end mail flow restored
What you receive
Clear findings, practical recommendations and hands-on support appropriate to the scope of the engagement.
Detailed findings
Root-cause analysis with relevant evidence, affected configuration and recommended actions.
Configuration changes
Implementation assistance with agreed policy, connector, routing or configuration changes where required.
Validation results
Confirmation that expected mail flow and relevant security controls behave correctly after remediation.
Knowledge transfer
Walkthrough of findings, changes and operational considerations with your messaging or security team.
Ongoing support options
Guidance for follow-up issues and agreed ongoing support arrangements where required.
Frequently asked questions
Common questions about our email security troubleshooting and support services.
What types of email issues do you help troubleshoot?
We can investigate supported email-security and mail-flow issues involving delivery, routing, connectors, SMTP/TLS, policies, authentication, platform integration and related operational behavior within the agreed scope.
Do you provide ongoing support or only one-time troubleshooting?
Both can be considered. Engagements may be focused on a specific incident or include agreed follow-up and ongoing operational support where that forms part of the scope.
Can you help with Proofpoint and Microsoft 365 integration issues?
Yes. We can investigate supported Proofpoint and Exchange Online integration issues including connectors, mail flow, routing, policy behavior, TLS and delivery evidence.
What information do you need to start an investigation?
Useful evidence can include affected sender and recipient addresses, timestamps, message IDs or headers, SMTP responses, message trace data, gateway logs, screenshots, recent changes and a clear description of the expected versus observed behavior.
Do you assist with SPF, DKIM and DMARC failures?
Yes, where the issue is within the agreed scope. We can review authentication results, DNS records, alignment, mail flow and related evidence to identify configuration or delivery problems.
Can you help with intermittent or hard-to-reproduce issues?
Yes. These investigations usually depend on precise timestamps, affected examples, message trace, gateway or SMTP evidence and comparison of successful versus failed events to isolate the relevant condition.
How quickly can you investigate an issue?
Timing depends on availability, urgency, scope, access and the evidence available. We confirm the expected investigation timing before work begins rather than promising a fixed response time for every environment.
How is a troubleshooting engagement scoped?
The scope depends on the symptoms, affected systems, business impact, available evidence and complexity of the environment. Requirements are reviewed first so the investigation approach and commercial scope can be agreed before work begins.
Need help with an email security issue?
Whether you are facing a delivery issue, an integration problem or a complex mail-flow failure, we can help you investigate the cause, apply the agreed remediation and validate expected behavior.
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