Can linking to PDF files in email cause bounces due to Mimecast or other security filters?

Summary

Linking to PDF files in emails can indirectly cause bounces due to security filters like Mimecast. The primary factors influencing this are the reputation of the hosting domain, the content of the PDF, and the accessibility of the link. Mimecast and other security filters scan the linked content and the linking domain, and may block emails if they detect a poor reputation, malicious content, or inaccessible resources. While linking bypasses attachment size limits, it doesn't circumvent content scrutiny. Adherence to RFC standards, maintaining a positive sender reputation, using reputable hosting, and scanning PDFs for malicious content are crucial for successful email delivery.

Key findings

  • Domain Reputation: The reputation of the domain hosting the PDF significantly impacts deliverability. Blacklisted or untrusted domains can lead to email rejections.
  • PDF Content: Spam filters scan the content within the PDF. Malicious content, spam-triggering keywords, or non-compliant elements can trigger filters.
  • Accessibility Matters: If links are not reachable from certain geographic locations, this can raise suspicion and lead to bounces.
  • Security Policies: Organizations configure security policies to block specific content types or URLs, impacting email delivery.
  • Linking vs Attachment: While linking circumvents size limits, it doesn't guarantee better deliverability; the link is still subject to content scanning.

Key considerations

  • Reputable Hosting: Use reputable and trusted hosting services for PDFs.
  • Content Scanning: Proactively scan PDFs for malicious content, spam triggers, and non-compliant elements.
  • Sender Reputation: Maintain a positive sender reputation by following email best practices.
  • Test Accessibility: Ensure PDFs are accessible from various geographic locations.
  • RFC Compliance: Adhere to RFC specifications for email formatting.

What email marketers say
11Marketer opinions

Linking to PDFs in emails does not directly cause bounces, but several factors can trigger spam filters and impact deliverability. These factors include the reputation of the domain hosting the PDF, the content within the PDF itself, and whether the links are reachable from various locations. Security filters such as Mimecast may block emails with links to untrusted or blacklisted sites. Link shorteners can also negatively impact deliverability. Using reputable hosting services, building a positive sender reputation, and ensuring clean, malware-free content are crucial.

Key opinions

  • Domain Reputation: The reputation of the domain hosting the PDF is a significant factor. Links to untrusted or blacklisted domains are more likely to be flagged as spam.
  • PDF Content: The content within the PDF is scanned and can trigger spam filters if it contains suspicious or malicious content.
  • Accessibility: If the linked PDF is not reachable from certain locations (e.g., due to regional restrictions), it can cause bounces as security scanners may interpret this as suspicious activity.
  • Attachment vs Link: While linking can bypass some attachment filters, the content is still subject to security checks. Using a link may not guarantee better deliverability than attaching the PDF.

Key considerations

  • Use Reputable Hosting: Host PDFs on reputable and trusted domains to avoid being flagged as suspicious.
  • Content Scrutiny: Ensure the PDF content is clean, free of malware, and does not contain spam-triggering keywords or phrases.
  • Monitor Sender Reputation: Maintain a positive sender reputation by adhering to email best practices and avoiding practices that could damage your sender score.
  • Avoid Link Shorteners: Using link shorteners can negatively impact deliverability. Prefer using the full, direct link to the PDF where possible.
  • Accessibility Testing: Verify that the PDF is accessible from various geographic locations to prevent accessibility-related bounces.
Marketer view

Email marketer from EmailGeek Forums User PDFExpert states that while PDF attachments can cause bounces linking to files also can do the same if the file is on a unsafe server.

November 2024 - EmailGeek Forums
Marketer view

Email marketer from EmailToolTester says that if you link to a blocked or blacklisted site, then yes that is an issue. But generally linking to a PDF is not as big an issue as it used to be.

December 2022 - EmailToolTester
Marketer view

Email marketer from Mailjet explains that while linking to a PDF may not directly cause bounces, the content within the PDF can trigger spam filters. Also, using link shorteners can negatively affect deliverability.

June 2021 - Mailjet
Marketer view

Email marketer from Email Geeks shares that the issue might be that the links are directly to a Google storage bucket public link, not necessarily the PDF itself.

June 2022 - Email Geeks
Marketer view

Email marketer from Gmass explains that it does not matter wether or not you link to the file of include it as an attachment, both can cause deliverability issues.

November 2024 - Gmass
Marketer view

Email marketer from Hubspot explains that similar to images if the content is not safe the email can be rejected. Even if you link to the image and do not host it directly on the email, it can be rejected.

September 2022 - Hubspot
Marketer view

Email marketer from Reddit user u/EmailPro shares that direct links to PDFs hosted on untrusted or new domains can be flagged as suspicious by spam filters. They recommend using a reputable hosting service and building a positive sending reputation.

October 2024 - Reddit
Marketer view

Email marketer from StackOverflow user LinkLover shares that the location that you link to is very important, make sure it is from a known reputable provider. Also make sure that PDF is clean and free of malware.

August 2021 - StackOverflow
Marketer view

Email marketer from Email Vendor Guide responds stating that linking to PDFs directly shouldn't cause deliverability problems, however the URL and the content of the PDF can be scanned and will cause issues depending on what it contains.

May 2021 - Email Vendor Guide
Marketer view

Email marketer from Email Geeks explains he found the cause: Some links on the customer's email are not reachable from certain locations, and he believes Mimecast scanners blocked it.

September 2022 - Email Geeks
Marketer view

Email marketer from Sendinblue shares that while directly linking to PDFs isn't inherently problematic, the content and reputation of the linked domain can influence spam filtering. They suggest monitoring sender reputation and ensuring content is relevant.

April 2023 - Sendinblue

What the experts say
3Expert opinions

Experts agree that linking to PDFs in emails can impact deliverability, primarily due to domain reputation and content security concerns. If the linked domain has a poor reputation or the PDF contains suspicious content, spam filters, including Mimecast, may flag the email. Additionally, blocking content analysis gateways from accessing the linked content can be interpreted as malicious activity and lead to rejection.

Key opinions

  • Domain Reputation Matters: A poor reputation of the linked domain can lead to emails being flagged as spam.
  • Content Analysis is Crucial: Suspicious or harmful content within the PDF can trigger spam filters.
  • Content Blocking Signals Malware: Preventing content analysis gateways from accessing the linked content can be a sign of malicious intent.
  • Generic Rejections Lack Detail: Mimecast's generic rejections don't provide detailed reasons, making troubleshooting more challenging.

Key considerations

  • Monitor Domain Reputation: Regularly check the reputation of domains used for hosting PDFs.
  • Scan PDF Content: Thoroughly scan PDFs for potentially harmful content before linking to them.
  • Avoid Blocking Gateways: Ensure content analysis gateways can access linked PDFs to avoid being flagged as malicious.
Expert view

Expert from Word to the Wise responds sharing that including links to domains with low reputations, or to content that is identified as spam can negatively affect email placement and deliverability, including linking to a PDF.

October 2021 - Word to the Wise
Expert view

Expert from Spam Resource shares that linking to PDFs can be problematic if the linked domain has a poor reputation or if the PDF itself contains suspicious content. Spam filters may flag these links as potentially harmful.

December 2022 - Spam Resource
Expert view

Expert from Email Geeks shares that blocking content analysis gateways from seeing the hostile content, while letting the recipients see it, seems like something malware would do. He also notes that the rejection is a generic Mimecast rejection.

June 2023 - Email Geeks

What the documentation says
4Technical articles

Technical documentation from various sources indicates that while linking to PDFs in emails can circumvent attachment size limits and some attachment filtering, it does not guarantee deliverability. Security policies configured by organizations, adherence to email format standards (RFC), and content scanning tools used by providers like Google Workspace and Microsoft Exchange Online Protection can still flag linked PDFs as malicious or non-compliant, leading to email rejections or filtering.

Key findings

  • Security Policy Enforcement: Organizations can configure security policies that block specific content types or URLs, affecting linked PDFs.
  • RFC Compliance: Emails not adhering to RFC specifications for formatting attachments and links can trigger security filters.
  • Content Scanning Persists: Linking to a PDF does not prevent content scanning by email providers; malicious content can still lead to filtering.
  • Size Limit Circumvention: Linking to a PDF allows bypassing attachment size limits imposed by email providers like Google Workspace.

Key considerations

  • Understand Recipient Policies: Be aware of the security policies of recipient organizations that may impact linked PDFs.
  • Ensure RFC Compliance: Adhere to RFC specifications for email formatting to avoid triggering filters.
  • Scan PDF Content Proactively: Thoroughly scan PDF content for malicious elements before including links in emails.
  • Optimize PDF Size: While linking bypasses size limits, optimize PDF size to improve user experience.
Technical article

Documentation from Google Workspace answers that Google Workspace has limits on attachment and message sizes. Linking to a PDF avoids the size limitations but the link could be checked by security tools.

November 2023 - Google Workspace
Technical article

Documentation from RFC Editor states that RFC specifications define standards for email formats, including how attachments and links should be handled. Non-compliant formatting may trigger security filters.

April 2024 - RFC Editor
Technical article

Documentation from Mimecast Knowledge Base explains that rejections due to security policies can occur when the content of the email (including linked content) violates the organization's configured rules. These rules can be configured to block certain content types or URLs.

February 2024 - Mimecast
Technical article

Documentation from Microsoft explains that PDFs, like other file types, can be blocked by Exchange Online Protection if they contain malicious content. Linking bypasses attachment filtering but the linked content could still be scanned.

July 2022 - Microsoft