Suped

What causes email deliverability issues for Gmail users with iCloud Private Relay?

Summary

iCloud Private Relay, while primarily designed to anonymize IP addresses and DNS requests for web browsing and app usage, has a significant impact on email marketing analytics, particularly for Gmail users. Most experts agree it does not directly interfere with email delivery via SMTP. However, it does mask a user's location and precise open times for emails viewed in webmail clients or links clicked through browsers that use the relay, leading to less accurate tracking data. Despite this, some email marketers have reported specific instances of deliverability issues, such as emails landing in spam or failing to arrive for Gmail users when Private Relay is active, even as direct sends to the same addresses are unaffected. These observed deliverability challenges may stem from factors like the reputation of the Private Relay domains themselves, user behavior when enabling the relay, or how Google's systems handle web-based interactions involving obscured IP addresses within Gmail. Ultimately, clarifying and resolving these nuanced interactions might necessitate input from both Apple and Google.

Key findings

  • Primary Impact on Tracking: iCloud Private Relay primarily affects the accuracy of email open and click tracking, masking user IP addresses, location data, and precise interaction times for emails viewed through web browsers or apps using the relay.
  • Limited Direct Deliverability: Many experts state that Private Relay does not directly interfere with standard email delivery protocols, SMTP, meaning it should not inherently cause emails to bounce or fail to arrive.
  • Anecdotal Deliverability Issues: Despite the general consensus, some email marketers have observed specific cases of emails to Gmail users being sent to spam or not delivered when iCloud Private Relay is active, while direct sends to the same addresses succeed.
  • Potential Indirect Factors: Possible explanations for observed deliverability issues include the reputation of the 'privaterelay.appleid.com' domains, potentially impacted by users employing them when distrusting senders, or how Google's systems might interpret obscured IP addresses for web-based interactions within Gmail.
  • Requires Vendor Resolution: Resolving specific deliverability anomalies related to Private Relay and Gmail would likely require collaboration or clarification from both Apple and Google.

Key considerations

  • Adjust Engagement Metrics: Email marketers must adjust to less precise IP-based data for open and click tracking, re-evaluating how they measure engagement, segment audiences, and personalize content for users on Apple devices with Private Relay enabled.
  • Monitor Gmail Deliverability: Senders should closely monitor deliverability to Gmail users, especially if a significant portion of their audience uses Apple devices, and investigate any unusual drops in inbox placement that might correlate with Private Relay usage.
  • Focus on Authentication and Reputation: Given concerns about the reputation of relay domains, maintaining strong sender authentication, such as SPF, DKIM, and DMARC, along with overall sender reputation, becomes even more critical to ensure emails are trusted regardless of intermediate IP masking.
  • Understand User Trust: Recognize that users might enable Private Relay when they have privacy concerns or distrust a sender, which could indirectly contribute to negative interactions that impact domain reputation.
  • Distinguish from MPP: Understand that iCloud Private Relay is distinct from Apple's Mail Privacy Protection, MPP. While both impact data collection, Private Relay focuses on web browsing IP obfuscation, whereas MPP specifically proxies email opens.

What email marketers say

10 marketer opinions

For Gmail users, iCloud Private Relay primarily affects how email engagement is measured, rather than directly preventing email delivery. It works by anonymizing a user's IP address when they browse content or interact with web-based elements, like clicking email links or loading images in their webmail client (such as Gmail accessed via Safari). This leads to less accurate data on recipient location and precise open times, impacting a marketer's ability to segment or personalize campaigns based on such details. While the consensus is that it doesn't cause emails to bounce, some marketers have observed specific instances where emails sent via Private Relay ended up in Gmail's spam folder or simply did not arrive, even as direct sends to the same addresses were successful. These particular deliverability challenges appear to be connected to the relay system itself, possibly due to how Google interprets traffic from these anonymized sources or the reputation associated with the 'privaterelay.appleid.com' domains.

Key opinions

  • Primary Impact on Tracking Accuracy: iCloud Private Relay primarily affects the accuracy of email open and click tracking for Gmail users by masking their IP addresses and thus obscuring geographic location and precise interaction times when emails are viewed in web browsers or apps using the relay.
  • Limited Direct Delivery Interference: Most sources indicate that iCloud Private Relay does not directly prevent email delivery or cause bounces via standard SMTP protocols; its effect is largely confined to the data collected post-delivery during user interaction.
  • Anecdotal Deliverability Issues Reported: Despite the primary impact being on tracking, some email marketers have observed specific cases where emails sent via Apple Private Relay landed in Gmail's spam folder or failed to arrive, while direct sends to the same Gmail addresses were successful.
  • Mechanism of Impact on Web Interactions: The relay works by anonymizing a user's IP address for web traffic, including when they click links from emails or load external content like images in a webmail client (e.g., Gmail in Safari) on an Apple device with Private Relay enabled.
  • Consequences for Marketing Strategies: The resulting data gaps impact a marketer's ability to perform precise audience segmentation, personalization based on location, and A/B testing that relies on granular IP-derived engagement insights.

Key considerations

  • Adjust Measurement Strategies: Email marketers must refine their approach to measuring engagement and attribution, as IP-based data for location and precise open times becomes unreliable for Gmail users interacting with emails via iCloud Private Relay.
  • Monitor Gmail Deliverability Closely: Despite the general consensus, specific reports of emails landing in spam or not arriving for Gmail users with Private Relay necessitate vigilant monitoring of deliverability metrics for this segment to detect any anomalies.
  • Reinforce Sender Reputation: Maintaining robust sender authentication-DKIM, SPF, and DMARC-and a strong overall sender reputation is paramount. This helps ensure emails are trusted and delivered even when the user's IP is anonymized by a relay service.
  • Leverage First-Party Data: To compensate for lost IP-based insights, marketers should prioritize collecting and utilizing first-party data, such as explicit preferences and purchase history, for segmentation and personalization.
  • Understand Private Relay's Purpose: Recognize that iCloud Private Relay is a privacy feature. Its use by subscribers underscores a preference for data anonymity, which should guide email program design toward more privacy-respecting practices.

Marketer view

Email marketer from Email Geeks shares a past client experience where emails sent via Apple Private Relay landed in Gmail's spam folder, whereas direct sends to the same Gmail address reached the inbox. She concluded that the issue was related to Apple's relay system, as the client had no problems sending directly to Gmail.

28 Aug 2021 - Email Geeks

Marketer view

Email marketer from Email Geeks explains that despite normal bounce rates, emails to Gmail users through iCloud Private Relay are not reaching inboxes or spam folders. He notes that direct sends to Gmail are unaffected and suspects the mail is being quarantined or sent to spam, referencing eDataSource data indicating poor placement for the privaterelay.appleid.com domain. He also shares Apple's feedback about missing MX and A records for his sender's domain, but questions why this would specifically impact Gmail Private Relay users and not result in visible bounces across all recipients.

11 Sep 2024 - Email Geeks

What the experts say

3 expert opinions

Experts widely agree that iCloud Private Relay is built for web browsing and does not directly interfere with email delivery, which relies on standard SMTP protocols. However, despite this consensus, discussions continue regarding indirect factors that could potentially impact email interactions for Gmail users. One perspective suggests that if issues were to arise, the reputation of the Private Relay domains, possibly influenced by user privacy choices, could be a contributing element. In such scenarios, Apple is expected to send a bounce notification if an email is rejected through the relay. Ultimately, resolving any persistent deliverability anomalies between Private Relay and Gmail would require direct engagement from both Apple and Google.

Key opinions

  • Web-Focused Service: iCloud Private Relay is explicitly designed for anonymizing web browsing traffic and masking IP addresses for apps, not for the direct handling or transmission of email via standard SMTP protocols.
  • No Direct Email Deliverability Impact: Most experts affirm that iCloud Private Relay does not inherently cause email deliverability issues for Gmail users by interfering with the fundamental mechanisms of email protocols, as it operates separately from how email is typically handled.
  • Indirect Reputation Concerns: Despite its primary function, some theories propose that the reputation of the Private Relay domains themselves, potentially stemming from user privacy choices or a lack of trust in a sender, could indirectly influence how associated web interactions are perceived by services like Gmail.
  • Bounce Mechanism: If an email were to be rejected when a user is interacting via iCloud Private Relay, Apple is expected to generate and send a bounce notification back to the sender, indicating the delivery failure.
  • Vendor Collaboration for Resolution: Any specific or ongoing deliverability challenges that appear to be related to iCloud Private Relay and Gmail would likely necessitate direct collaboration and clarification from both Apple and Google, as they control the respective systems.

Key considerations

  • Reinforce Core Deliverability Practices: Since iCloud Private Relay is primarily designed for web traffic and not for direct email delivery, it is crucial to maintain rigorous adherence to fundamental email deliverability best practices, including strong sender authentication like SPF, DKIM, and DMARC, as well as robust list hygiene.
  • Monitor for Anomalies: Despite the general consensus that it does not directly impact email delivery, closely observe deliverability to Gmail recipients, particularly those using Apple devices. This vigilance helps detect any unexpected or indirect issues, even if direct causation is generally dismissed.
  • Understand Relay Domain Reputation Nuance: While Private Relay does not directly handle email, be aware of discussions regarding the potential reputation of its anonymized IP addresses. This could indirectly affect overall web-based email interaction signals, particularly if users enable the relay due to distrust of senders.
  • Acknowledge Vendor Role: Recognize that ultimate clarification or resolution for any perceived interaction-based deliverability issues between iCloud Private Relay and Gmail rests with direct communication and collaboration between Apple and Google.

Expert view

Expert from Email Geeks explains that if email is rejected via iCloud Private Relay, Apple should send a bounce. She notes that only Apple and Google can truly resolve these specific issues and suggests warning users about potential delivery problems to Gmail via Private Relay. Atkins adds that Google usually does not simply drop mail, nor does Apple. She states that iCloud Private Relay domains likely have a questionable reputation because users often employ them when they do not trust the sender, leading to negative interactions that can harm the relay domain's reputation. She clarifies that Apple would keep the connection open to report rejections if Google failed and suggests that both the relay's reputation and potential DNS issues could contribute to delivery problems.

7 Oct 2021 - Email Geeks

Expert view

Expert from Word to the Wise explains that Apple's iCloud Private Relay is designed specifically for web browsing traffic, not for email. Therefore, it does not directly impact or cause email deliverability issues for Gmail users, as email delivery uses standard SMTP protocols which are unaffected by Private Relay.

9 May 2023 - Word to the Wise

What the documentation says

3 technical articles

iCloud Private Relay does not inherently create deliverability problems for emails sent to Gmail users; rather, its influence lies in obscuring recipient data. The service is designed to anonymize a user's IP address and DNS requests when they interact with web content through apps or browsers like Safari. While email delivery via SMTP remains unaffected, this masking prevents senders from accurately collecting IP-based information when a user loads images or clicks links within an email in their Gmail web interface. Consequently, traditional IP-dependent functions such as geo-targeting, fraud detection, and security checks become less precise, leading to challenges in data-driven segmentation and personalization rather than direct delivery failures.

Key findings

  • No Direct Delivery Block: iCloud Private Relay does not directly impede the fundamental delivery of emails to Gmail inboxes, as its function is separate from core SMTP protocols.
  • IP Anonymization Post-Delivery: The service masks a user's IP address specifically when they interact with email content, for example, loading images or clicking links, through a web browser or app utilizing the relay.
  • Data Accuracy Impairment: This IP obfuscation leads to less accurate data regarding recipient location, precise open times, and engagement metrics derived from IP addresses.
  • Impact on IP-Dependent Services: Functions like IP-based geo-targeting, fraud detection, and security checks within web-based email interactions are hindered by the masked IP addresses.

Key considerations

  • Rethink Engagement Measurement: Marketers must adapt their strategies for measuring email engagement and user behavior, moving beyond reliance on precise IP-based data for Gmail users with Private Relay enabled.
  • Prioritize First-Party Data: To maintain robust personalization and segmentation, emphasize collecting and leveraging first-party data, such as explicit preferences and purchase history, which are unaffected by IP masking.
  • Maintain Deliverability Best Practices: Continue to focus on strong sender reputation, list hygiene, and robust authentication-SPF, DKIM, DMARC-as these are the primary drivers of email deliverability, independent of Private Relay.
  • Adjust Expectations for IP-Based Analytics: Understand that detailed IP-based geographical and real-time open data may be significantly less reliable for a segment of your audience, requiring a shift in how these insights are used.

Technical article

Documentation from Apple Support explains that iCloud Private Relay, when enabled, helps protect a user's IP address and DNS requests, routing them through two separate internet relays. While not directly impacting email delivery, this mechanism means that any email content loaded within a web browser or app using Private Relay would obscure the user's true IP address, making traditional IP-based geo-targeting or fraud detection less accurate for senders.

26 Sep 2022 - Apple Support

Technical article

Documentation from Google Support, in relation to privacy features, generally implies that any third-party IP obfuscation service like iCloud Private Relay would prevent their systems from seeing the user's true IP address when interacting with web services. While Gmail's core email delivery doesn't rely on the recipient's IP in transit, the user's browsing IP, if masked by Private Relay, could affect how certain web-based interactions (like loading images in Gmail's web interface) are logged, potentially impacting IP-based security checks or personalization.

4 Apr 2023 - Google Support

Start improving your email deliverability today

Get started