Suped

Summary

SPF verification failures for emails forwarded to services like Gmail are a common challenge rooted in how SPF works. SPF checks the IP address of the mail server that directly delivers the email to the recipient's server against the original sender's SPF record. When an email is forwarded, the forwarding server acts as this intermediary sender, and its IP address is almost certainly not listed as an authorized sender in the original domain's SPF record, leading to an SPF failure. This fundamental incompatibility often results in DMARC failures as well, particularly if SPF alignment is a requirement for the domain's DMARC policy. While Sender Rewriting Scheme (SRS) is designed to mitigate this issue by modifying the envelope sender, forwarding services that do not implement SRS will consistently cause SPF failures. In specific instances, the forwarding service itself might be the source of rejection, possibly relaying rejections from the final destination or misreporting bounce reasons with unclear headers, emphasizing the need to consult the forwarding service for diagnostic information.

Key findings

  • Inherent SPF-Forwarding Conflict: SPF inherently conflicts with email forwarding. SPF validates the IP address of the last mail server sending the email against the 'Mail From' (envelope sender) domain. When an email is forwarded, the forwarding server becomes this 'last hop,' and its IP address will not be authorized in the original sender's SPF record, causing SPF to fail.
  • DMARC Failure Consequence: SPF failures due to forwarding frequently lead to DMARC failures, especially if the DMARC policy for the original domain requires SPF alignment and has an enforcement policy like 'p=reject'.
  • SRS as the Solution: Sender Rewriting Scheme (SRS) is the primary technical solution to prevent SPF failures in forwarded emails. It works by rewriting the 'Return-Path' (envelope sender) address to include the forwarding service's domain, allowing SPF checks to pass at the receiving end.
  • DKIM's Resilience to Forwarding: Unlike SPF, DKIM is generally more robust against email forwarding. A DKIM signature, once applied by the original sender, remains valid through forwarding, provided the message content is not altered by the forwarding process.
  • Forwarding Service Specific Issues: In some cases, the forwarding service itself may be the direct cause of the rejection, potentially due to its own policies (e.g., quietly requiring DKIM), internal rate limiting, or misreporting bounce reasons. Such scenarios may involve confusing bounce messages or 'messed about with' headers.

Key considerations

  • Contact Forwarding Service: For specific issues, like those involving forwardemail.net, it is critical to contact the forwarding service's support team. They possess the necessary logs to definitively clarify whether they rejected the message themselves or if it was a relayed rejection from the final destination, such as Gmail.
  • Verify SRS Implementation: If you are utilizing an email forwarding service, confirm that it implements Sender Rewriting Scheme (SRS). Without SRS, forwarded emails are highly likely to encounter SPF failures, as SRS is designed to address this fundamental incompatibility.
  • Analyze Bounce Messages and Headers: Be aware that bounce messages and email headers from forwarding services can sometimes be misleading or 'weird,' potentially misreporting the actual reason for rejection or tunneling a rejection from the final recipient server. Thorough analysis of headers, or direct vendor communication, is often necessary for accurate diagnosis.
  • Original SPF Policy Impact: The SPF policy of the original sending domain, particularly a strict '-all' (hard fail) policy, can explicitly instruct receiving servers not to accept emails where SPF fails, making issues with forwarding more pronounced.
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What email marketers say

11 marketer opinions

The fundamental reason for SPF verification failures when emails are forwarded, especially to major providers like Gmail, lies in SPF's design. SPF authenticates the sender by checking the IP address of the mail server that directly transmits the email to the recipient's server against the original domain's SPF record. When an email is forwarded, the forwarding service's server becomes this intermediary 'last hop,' and its IP address almost invariably does not align with the original sender's authorized IPs in their SPF record. This mismatch results in an SPF authentication failure, which often cascades into DMARC failure if the domain's policy mandates SPF alignment. While Sender Rewriting Scheme (SRS) can overcome this by altering the Return-Path, its absence on a forwarding service guarantees SPF will break. Furthermore, diagnosing these failures can be complex, as some forwarding services may generate misleading bounce messages or even be the direct cause of the rejection themselves, necessitating direct communication with their support for clear insights.

Key opinions

  • SPF's Last Hop Check: SPF's design dictates that it validates the IP address of the *last* mail server to transmit the email against the 'Mail From' (envelope sender) domain in the sender's SPF record. This fundamental mechanism is the root of the issue with forwarding.
  • IP Mismatch with Forwarding: When an email is forwarded, the forwarding server's IP address is the one presented for the SPF check. This IP is almost never authorized in the original sender's SPF record, causing the SPF validation to fail, commonly resulting in a softfail.
  • Sender Rewriting Scheme (SRS) Necessity: To prevent SPF failures, forwarding services must implement SRS. SRS rewrites the 'Return-Path' (envelope sender) address to include the forwarding service's domain, allowing SPF to pass at the receiving end by correctly associating the forwarding server's IP.
  • DKIM's Resilience: Unlike SPF, DKIM signatures typically remain valid through forwarding processes, provided the message content is not altered. This makes DKIM a more robust authentication method in scenarios involving email forwarding, as the cryptographic signature persists.
  • Potential for Misleading Bounces: Some forwarding services may issue confusing bounce messages, misattribute rejection reasons, or 'tunnel' rejections from the final recipient server. This can make accurate diagnosis difficult without direct insight into the forwarding service's internal logs.

Key considerations

  • Assess Forwarding Service Capabilities: Before relying on an email forwarding service, confirm its commitment to implement Sender Rewriting Scheme (SRS). The absence of SRS is a guaranteed path to SPF failures for forwarded mail, significantly impacting deliverability.
  • Understand DMARC Alignment Impact: Recognize that SPF failures due to forwarding will often lead to DMARC failures if your domain's DMARC policy requires SPF alignment, especially for domains with a 'p=reject' or 'p=quarantine' policy, which can block legitimate emails.
  • Investigate Forwarding Service Specifics: If bounces occur, particularly from services like forwardemail.net, contact their support. They can clarify if they quietly enforce other requirements, like DKIM, or if their bounce messages are simply relayed rejections from the final destination, providing crucial diagnostic information.
  • Differentiate SPF 'Softfail': Be aware that forwarded emails often result in an SPF 'softfail' rather than a hard fail. While a softfail suggests the message might be legitimate, it still indicates an authentication issue that can impact deliverability, particularly when DMARC is active or recipient servers are strict.

Marketer view

Marketer from Email Geeks states that the mx2.forwardemail.net server indicated it rejected the mail due to SPF failure, suggesting forwardemail.net is the source of the rejection. He explains the bounce flow, where Google receives the 550 message from forwardemail.net and then generates the human-readable bounce. He also points out that the message headers have been "messed about with," creating confusion, and suggests the SPF mention might be a "tunneled rejection." He strongly advises contacting forwardemail.net support for diagnosis.

31 Jul 2024 - Email Geeks

Marketer view

Marketer from Email Geeks confirms that forwardemail.net likely bounced the email, potentially as a relay from the final system, but questions if SRS should have passed. He suggests that forwardemail.net might be quietly requiring DKIM, even if the bounce code indicates an SPF failure, especially when no Google DKIM key is found. He emphasizes that only forwardemail.net can provide definitive answers from their logs.

1 Dec 2021 - Email Geeks

What the experts say

3 expert opinions

SPF verification failures for emails forwarded to services such as Gmail are primarily due to the fundamental design of SPF. SPF validates the IP address of the server directly delivering the email against the envelope sender's domain. When an email passes through a forwarding service, that service's server becomes the new sender for the next hop. Since its IP address is almost certainly not listed as an authorized sender in the original domain's SPF record, the SPF check inevitably fails. This issue is compounded when the original sending domain employs a strict SPF policy, like '-all,' which explicitly instructs recipient servers to reject emails that fail SPF. Furthermore, diagnosing these failures can be complex, as some forwarding services may obscure the true reason for rejection, either by misreporting bounce messages or by relaying rejections from the final destination without clear indication, making direct communication with the forwarding service essential for precise troubleshooting.

Key opinions

  • SPF's IP-based Validation: SPF authenticates the message's envelope sender by verifying the IP address of the server that directly transmits the email to the recipient's mail server.
  • Forwarding Breaks IP Authorization: When an email is forwarded, the forwarding service's server acts as the sender for the next hop. Its IP address will almost certainly not be authorized by the original sending domain's SPF record, causing the SPF check to fail.
  • Impact of Strict SPF Policies: An original sending domain with a strict SPF policy, such as '-all,' explicitly instructs receiving mail servers not to accept emails where SPF verification fails, exacerbating deliverability issues for forwarded mail.
  • Forwarding Service's Diagnostic Challenges: A forwarding service might directly block messages or relay rejections from the final destination without clear communication, often presenting confusing bounce messages or 'weird' headers that complicate accurate diagnosis of the underlying cause.

Key considerations

  • Engage the Forwarding Service: For specific SPF failures related to forwarded emails, it is crucial to contact the email forwarding service directly. They have the necessary logs to clarify whether they rejected the message themselves or if it was a relayed rejection from the final destination, like Gmail.
  • Scrutinize Bounce Messages and Headers: Be aware that bounce messages and email headers from forwarding services can sometimes be misleading or 'weird,' potentially misreporting the actual reason for rejection or tunneling a rejection from the final recipient server. Thorough analysis of headers, or direct vendor communication, is often necessary for accurate diagnosis.
  • Understand SPF '5321.from' Context: When diagnosing SPF failures for forwarded mail, remember that 'the domain' referenced in error messages typically refers to the 5321.from address, which is the envelope sender that SPF is validating.

Expert view

Expert from Email Geeks explains that email forwarding service forwardemail.net appears to be blocking SPF failures or is relaying a rejection from the final destination. She notes that the original sending domain, truefans.fm, has a -all SPF record which explicitly tells Google not to allow forwarding. She clarifies that "the domain" in the error refers to the 5321.from address. Laura suggests forwardemail.net might be misreporting the bounce reason, potentially due to Google's rate limiting, describing the bounce message as "bad" and headers as "weird." She consistently advises contacting the vendor, forwardemail.net, for definitive answers because they have the logs and can clarify if they rejected the message or if Gmail did and it was relayed.

23 Jan 2023 - Email Geeks

Expert view

Expert from Spam Resource explains that SPF verification failures for forwarded emails are unavoidable because SPF authenticates the message envelope sender. When an email is forwarded, the forwarding server becomes the sender, causing SPF to fail since the original sender's SPF record won't authorize the forwarding server's IP address.

29 Jul 2024 - Spam Resource

What the documentation says

6 technical articles

Email authentication via SPF frequently fails for messages forwarded to providers like Gmail because of how SPF validates the sending server. SPF verifies the IP address of the mail server that establishes the direct connection against the original sender's SPF record. When an email is forwarded, the forwarding server takes on the role of the direct sender, presenting its own IP. This IP address will not be authorized within the original sender's SPF record, causing the verification check to fail, often resulting in a 'softfail' or 'fail' status for the original domain. The Sender Rewriting Scheme (SRS) was developed as a mechanism to address this by altering the envelope sender, but its absence on forwarding services ensures SPF failure.

Key findings

  • SPF's Connection-Based Check: SPF authenticates by checking the IP address of the server directly connecting and sending the email against the envelope sender's domain.
  • Forwarding's IP Mismatch: When an email is forwarded, the forwarding server's IP becomes the connecting IP, which almost certainly does not match any authorized IPs in the original sender's SPF record.
  • Resulting SPF Failure States: This mismatch typically causes SPF verification to result in a 'softfail' or 'fail' for the original sending domain when emails are forwarded without proper handling.
  • SRS as Mitigation: The Sender Rewriting Scheme (SRS) is specifically designed to prevent these SPF failures by rewriting the envelope sender address to reflect the forwarding server.
  • Impact of Non-SRS Forwarders: Forwarding services that do not implement SRS will consistently lead to SPF failures because the fundamental IP mismatch issue remains unaddressed.

Key considerations

  • Verify SRS for Forwarding: If using an email forwarding service, confirm its support and implementation of Sender Rewriting Scheme (SRS) to ensure SPF authentication passes.
  • Anticipate SPF Failure Without SRS: Understand that without SRS, forwarded emails are highly prone to SPF 'softfail' or 'fail' outcomes, which can negatively impact deliverability.
  • Consult Foundational SPF Specs: Recognize that the issue of forwarding causing SPF failures is directly addressed in the core SPF specification (RFC 7208), highlighting its known and expected behavior.

Technical article

Documentation from Google Workspace explains that SPF is checked against the IP address of the last mail server to send the message. When an email is forwarded, the forwarding server acts as the last hop, and its IP address will not match the SPF record of the original sender's domain, leading to an SPF failure for forwarded emails to Gmail.

28 Aug 2022 - Google Workspace Admin Help

Technical article

Documentation from Microsoft Learn explains that SPF checks the envelope sender against the connecting IP address. When an email is forwarded, the forwarding server's IP becomes the connecting IP, which doesn't match the original sender's SPF record. This causes SPF to fail, and without Sender Rewriting Scheme (SRS), forwarded emails often result in SPF 'softfail' or 'fail' for the original domain.

16 Sep 2021 - Microsoft Learn

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