Can I email users who have Apple's private relay email addresses?

Yes, you can email users who have Apple's Private Relay email addresses. The relay system is designed to forward emails to the user’s true inbox. The challenge often lies in deliverability, as some Mailbox Providers, like Gmail, may apply stricter filtering to emails coming through these relay domains, perceiving them differently than direct sends.

Why are there no bounce messages if emails are not being delivered?

When emails to iCloud Private Relay users with Gmail addresses disappear without bounces, it often indicates that Apple’s relay successfully accepts the email , but the final delivery to Gmail is silently filtered. This could mean the email is quarantined, sent to spam, or otherwise suppressed by Gmail’s internal systems, without generating a rejection notice back to the original sender.

Does iCloud private relay affect my overall sender reputation?

iCloud Private Relay itself doesn't directly impact your sender reputation, as your emails are still authenticated with your domain. However, if emails sent via Private Relay consistently land in spam or are unengaged with, it can indirectly affect the perceived reputation of the relay domain, which in turn might make Gmail more wary of traffic from those relays affecting your deliverability to those specific recipients.

How can I effectively test deliverability to iCloud private relay addresses?

To test deliverability, set up a Gmail account and enable iCloud Private Relay with it. Send test emails from your platform to this Private Relay address. Monitor your internal sending logs for any bounces, and crucially, check the Gmail inbox, spam, and promotions folders directly. This hands-on testing is often the most reliable way to confirm deliverability.

What email authentication standards are most important for deliverability with private relay?

The most important email authentications are SPF, DKIM, and DMARC. These records prove your domain's legitimacy and ensure that emails haven't been forged or altered. Proper implementation provides a strong trust signal to Mailbox Providers like Gmail, making it less likely for your emails to be flagged, even when they pass through intermediary services like Private Relay.

What causes email deliverability issues for Gmail users with iCloud Private Relay? - Technical - Email deliverability - Knowledge base

Many senders are finding that their emails sent to Gmail users who have iCloud Private Relay enabled are facing significant deliverability challenges. While emails to other providers seem to arrive without a hitch, these specific messages often disappear, never reaching the inbox or even the spam folder.

The perplexing part is that there are no clear rejections or bounces on the sender's end, making it difficult to diagnose the problem using traditional methods. We’ve seen instances where signing up for services with an Apple Private Relay email address results in emails simply not arriving, despite the sender having a good reputation for direct Gmail recipients.

The nature of iCloud private relay and its impact

iCloud Private Relay is an Apple privacy feature designed to protect a user’s internet traffic by routing it through two separate internet relays. This process masks their IP address and hides their browsing activity from network providers and websites. For email, this includes the Hide My Email service, which creates unique, random email addresses that forward to the user's actual inbox.

While beneficial for user privacy, this anonymization introduces complexity for email deliverability. Since the original sender’s IP address and potentially the recipient’s true email address are obscured, it complicates the traditional trust signals that Mailbox Providers (MBPs) use to assess incoming mail. This can lead to increased scrutiny from sophisticated filtering systems, such as those used by

Gmail.

The core issue isn't necessarily a direct incompatibility, but rather how Gmail's advanced filters interpret email traffic coming from

Apple's relay domains. It’s a challenge of maintaining trust and transparency in a system built for privacy, making it harder for legitimate emails to bypass spam filters.

Standard email delivery

Direct connection: Your Mailbox Provider directly connects to the recipient’s Mailbox Provider.
IP visibility: The recipient's Mailbox Provider sees your sending IP address directly.

iCloud private relay delivery

Relayed connection:Apple's servers act as an intermediary, forwarding the email.
IP obscured: The recipient's Mailbox Provider sees an Apple Private Relay IP address, not yours.

The core issue isn't necessarily a direct incompatibility, but rather how Gmail's advanced filters interpret email traffic coming from Apple's relay domains. It’s a challenge of maintaining trust and transparency in a system built for privacy, making it harder for legitimate emails to bypass spam filters.

Why Gmail might react differently

While

Gmail doesn't typically drop mail on the floor without a bounce or rejection notice, emails routed through Private Relay might be subjected to stricter filtering. This can result in them landing in the spam folder, promotions tab, or being quarantined, rather than outright rejected. This behavior is rooted in Gmail’s approach to sender reputation and security.

The anonymous nature of Private Relay (and the `privaterelay.appleid.com` domain) means that Gmail can’t fully assess the sender based on traditional IP and domain reputation signals. If users employ these addresses for sign-ups where they have low trust, their subsequent actions (or inactions) might negatively impact the perceived reputation of the relay domain. This, in turn, can lead to your emails being flagged as suspicious, even if your own sending domain has an excellent reputation.

It’s a subtle but critical distinction from a direct rejection. The emails might be technically delivered to

Apple's relay, but then face obstacles when Apple attempts to forward them to Gmail, potentially due to the relay domain's reputation or specific filtering rules applied by Gmail to traffic originating from these proxy services.

Gmail's filtering with private relay

Gmail's filtering algorithms prioritize user safety and inbox relevance. When emails arrive via a privacy relay service, the direct sender information (like IP reputation) is masked. This can lead to increased skepticism from

Gmail's systems, especially if the aggregated reputation of the relay domain itself is not consistently strong. Emails might not bounce, but could be silently filtered or dropped, leaving senders unaware of the problem.

Diagnosing elusive deliverability failures

The absence of traditional bounce messages is a key indicator of this unique problem. Unlike typical rejections that provide diagnostic codes, Apple's Private Relay often holds the connection open while attempting delivery to the final recipient. If that final delivery to Gmail fails, the lack of a clear bounce back to the original sender creates a deliverability black hole.

While unusual for Gmail to simply drop mail, it's crucial to investigate potential underlying technical issues that could be exacerbated by the relay process. For example, some users have reported that missing MX or A records for the sending domain could cause delivery issues, even if other providers seem unaffected. This suggests that Gmail's parsing of DNS information, especially when dealing with proxied traffic, might be more stringent.

To accurately diagnose, you need to go beyond bounce reports. Implement granular logging, conduct extensive inbox placement tests using Private Relay addresses with Gmail as the final destination, and actively seek feedback from affected users. This will help confirm if emails are indeed being silently filtered or outright rejected at the final leg of delivery. This is where Google Postmaster Tools can provide valuable insights.

Check MX and A recordsbash

dig MX yourdomain.com
dig A yourdomain.com

Strategies for improving deliverability

The first step to mitigating these issues is ensuring your email authentication records are impeccable. This means properly configuring SPF, DKIM, and DMARC. While these don't directly resolve Private Relay's anonymization, they establish your domain's legitimacy, giving Gmail fewer reasons to flag your messages, even when they come through an intermediary.

Beyond technical configurations, maintaining a stellar sender reputation is paramount. Focus on sending highly engaged content to a clean, opted-in list. Minimize spam complaints and unengaged recipients. A strong sender reputation signals to Gmail that your emails are valued, making it more likely they’ll bypass filters, even if they arrive via a private relay. For more strategies, explore how to fix Gmail deliverability issues.

Finally, consider proactive communication. If you know a segment of your audience uses Private Relay, you might include a note during sign-up or in your welcome email, advising them to check their spam or promotions folders if they don’t see your messages. This sets expectations and empowers users to find your emails, reducing support tickets and improving overall engagement.

Authentication Method	Role	Impact on Private Relay Deliverability
SPF	Authorizes sending IPs	Ensures Apple's relays are authorized, reducing rejections.
DKIM	Verifies email content integrity	Confirms messages haven't been tampered with in transit.
DMARC	Enforces SPF/DKIM alignment and reporting	Provides visibility into how Gmail processes your emails.

Views from the trenches

Best practices

Implement robust DMARC policies to assert sending domain legitimacy.

Segment your audience by email provider to identify patterns unique to Gmail Private Relay users.

Educate users about checking spam folders if they opt for Private Relay addresses.

Common pitfalls

Assuming normal bounce rates mean successful delivery, especially with Private Relay.

Overlooking subtle DNS misconfigurations that could disproportionately affect relayed mail.

Failing to adapt engagement metrics to account for Private Relay’s impact on open tracking.

Expert tips

Closely examine email headers for clues when messages go missing, looking for any intermediary reports.

If your domain’s MX and A records are not perfectly aligned, it can sometimes cause issues with stricter receivers like Gmail through a relay.

Consider that the reputation of the private relay domains themselves can affect deliverability, independent of your own sender reputation.

Marketer view

Emails sent to Gmail users through iCloud Private Relay are experiencing deliverability issues, often not reaching the inbox, spam, or any other folder, despite normal bounce rates. This behavior is specific to Gmail, as other providers receive emails correctly.

2025-03-03 - Email Geeks

Expert view

Apple should typically send a bounce notification if an email is rejected, and it is unusual for Gmail to completely drop mail. Senders should consider warning users who sign up with Apple Private Relay addresses about potential delivery issues to Gmail.

2025-03-03 - Email Geeks

Key takeaways and next steps

Navigating email deliverability to Gmail users with iCloud Private Relay requires a nuanced approach. It’s not always about outright rejections, but often about subtle filtering that prevents emails from reaching the desired inbox. By understanding the privacy mechanisms at play, rigorously upholding email authentication standards, and actively monitoring deliverability, you can significantly improve your chances of reaching these recipients.

Remember, the goal is to build trust with Mailbox Providers, even when user privacy tools introduce new layers of complexity. Persistence in testing and adapting your email strategy will be key to success.