Why am I seeing iCloud email timeout errors?

Summary

iCloud email timeout errors are multi-faceted, stemming from potential issues within iCloud's infrastructure (server overload, greylisting), network configurations (MTU size), and sender practices. These practices include DNS resolution problems, SMTP protocol adherence, network issues like mail loops, sending volumes/rates, and sender reputation/authentication. Issues from email content (large email sizes) and list management are also contributing factors. Troubleshooting involves checking iCloud's system status, verifying DNS records, implementing proper SMTP standards, monitoring network paths and mail configurations, ensuring proper authentication, throttling sending volumes, managing sender reputation, optimizing email size, warming IP addresses, using double opt-in, and handling greylisting retries appropriately.

Key findings

  • iCloud Infrastructure: iCloud's infrastructure can be overwhelmed, and greylisting can cause retries to not function as expected.
  • Network Configuration: Incorrect MTU settings and other network issues, including DNS and SMTP problems, cause timeouts.
  • Sending Practices: Sending practices like exceeding sending limits, high sending volumes, and not warming IP addresses contribute to timeout errors.
  • Sender Reputation: Poor sender reputation, being blacklisted, and lack of email authentication trigger timeouts.
  • Email Content: Large email sizes, particularly with attachments, lead to timeout errors.
  • List Management: Lack of double opt-in and resultant effects have a negative impact.

Key considerations

  • Check iCloud Status: Monitor Apple's System Status page for iCloud outages.
  • Verify DNS Settings: Use tools to verify your DNS records.
  • Review Sending Volume: Implement rate limiting.
  • Authenticate Email: Use SPF, DKIM, and DMARC.
  • Warm-Up IPs: If using a new IP, start slow and ramp up.
  • Handle Greylisting: Make sure your server supports retries.
  • Reduce Email Size: Optimize images and attachments.
  • Double Opt-In: Use double opt-in lists.
  • MTU Size: Make sure your MTU Size is not too big.

What email marketers say
11Marketer opinions

iCloud email timeout errors can stem from a variety of factors, including issues on iCloud's end (server overload), sending practices (lack of authentication, exceeding sending limits, poor sender reputation, blacklisting, large email sizes, not warming IP addresses, high sending volumes), and recipient list quality (lack of double opt-in). Several marketers have reported experiencing these issues, sometimes with no discernible pattern. Troubleshooting involves ensuring proper email authentication, respecting sending limits, maintaining a good sender reputation, avoiding blacklists, optimizing email size, warming up IP addresses, rate-limiting email sends, using double opt-in, and monitoring system status.

Key opinions

  • iCloud Server Issues: iCloud's servers may be overwhelmed, causing temporary timeout errors.
  • Email Authentication: Lack of SPF, DKIM, and DMARC records can lead to stricter spam filtering and timeouts.
  • Sending Limits: Exceeding iCloud's sending limits can result in timeouts; throttling is recommended.
  • Sender Reputation: A poor sender reputation can trigger timeouts; monitoring and improvement are crucial.
  • Blacklisting: Being blacklisted can cause timeout errors; checking and removal are necessary.
  • Email Size: Large email sizes, especially attachments, can lead to timeouts; compression is advised.
  • IP Warming: Not warming up new IP addresses can affect deliverability and cause timeouts.
  • Sending Volume: High volumes of email sent too quickly can be rate-limited, causing timeouts.
  • Double Opt-in: Not using double opt-in may result in lower engagement and higher timeout rates.

Key considerations

  • Check System Status: Monitor Apple's System Status page for any reported iCloud Mail issues.
  • Authenticate Sending Domain: Ensure your sending domain is properly authenticated with SPF, DKIM, and DMARC.
  • Monitor Sender Score: Regularly monitor your sender score and take steps to improve it.
  • Check for Blacklisting: Verify if your IP or domain is on any email blacklists and request removal if needed.
  • Optimize Email Size: Compress images and reduce overall email size to improve sending reliability.
  • Warm-Up IP Addresses: Gradually warm up new IP addresses by sending smaller volumes to engaged recipients first.
  • Rate Limit Email Sends: Control the volume of emails sent within a specific timeframe.
  • Implement Double Opt-in: Use double opt-in to ensure recipients genuinely want to receive your emails.
  • Review Sending Practices: Assess your sending practices to make sure that you are a safe sender.
Marketer view

Marketer from Email Geeks confirms experiencing the same iCloud timeouts starting on February 7 and still persisting.

February 2022 - Email Geeks
Marketer view

Email marketer from EmailOnAcid Forum shares that iCloud timeouts might stem from poor sender reputation. They recommend monitoring your sender score and taking steps to improve it, such as cleaning your email list and engaging with recipients.

January 2022 - EmailOnAcid Forum
Marketer view

Email marketer from Hubspot answers that you should be using double opt-in when collecting email addresses, as this is a clear indication that this user wants to recieve your email messages. This should reduce the liklihood of timeouts.

January 2025 - Hubspot
Marketer view

Email marketer from Litmus says that issues can come from not warming your ip addresses. They encourage senders to slowly warm up new ip addresses on different lists before sending bulk emails.

October 2024 - Litmus
Marketer view

Email marketer from Stack Overflow explains that iCloud timeout errors can be caused by exceeding sending limits. He recommends throttling email sending to stay within iCloud's limits. He also suggests checking the size of attachments, as large files may cause timeouts.

August 2024 - Stack Overflow
Marketer view

Email marketer from Reddit suggests that iCloud email timeout errors can occur due to strict spam filtering. They recommend ensuring your sending domain is properly authenticated with SPF, DKIM, and DMARC records.

October 2023 - Reddit
Marketer view

Email marketer from Quora suggests that iCloud email timeout errors can arise from blacklisting. Check if your IP or domain is on any major email blacklists and take steps to be removed if listed.

July 2022 - Quora
Marketer view

Marketer from Email Geeks shares that they also experienced iCloud timeout errors and contacted iCloud's team, who responded that they had investigated the report and made appropriate changes. They were asked to resend and report if the issue persists.

October 2023 - Email Geeks
Marketer view

Email marketer from Mailjet support shares that large email sizes can cause timeouts. They advise compressing images and reducing the overall email size to improve sending reliability.

December 2023 - Mailjet
Marketer view

Marketer from Email Geeks says that they are also running into iCloud timeout errors with no discernible pattern, despite most emails to private relay addresses being sent without issue. The issue has been ongoing for about a week.

August 2022 - Email Geeks
Marketer view

Email marketer from Sendgrid answers that rate limiting your email sends is important, as high volumes of email sent too quickly will likely be affected by rate limiting.

April 2021 - Sendgrid

What the experts say
3Expert opinions

iCloud email timeout errors can arise from iCloud's infrastructure being overwhelmed, causing ESPs to exceed capacity. Greylisting, a temporary rejection tactic used by iCloud, can also lead to timeout errors if sending servers don't properly handle retries. Furthermore, incorrect network configurations, particularly related to MTU size, may contribute to the problem.

Key opinions

  • iCloud Overload: iCloud's infrastructure might be overwhelmed, leading to timeout errors due to capacity issues.
  • Greylisting: iCloud's use of greylisting can cause timeout errors if sending servers do not properly implement retry mechanisms.
  • MTU Size: Incorrect network configurations, especially related to MTU size, can result in timeout errors.

Key considerations

  • Infrastructure Capacity: Consider iCloud's capacity limitations when sending emails, particularly during peak periods.
  • Retry Mechanisms: Ensure your sending server correctly implements retry mechanisms to handle greylisting.
  • MTU Configuration: Check and adjust MTU settings on your server to ensure compatibility with iCloud's network requirements.
Expert view

Expert from Word to the Wise explains that greylisting (temporary rejection) by the receiving server, often used by iCloud, can cause apparent timeout errors if retries are not handled properly by the sending server. They suggest ensuring your sending server correctly implements retry mechanisms as per SMTP standards.

December 2022 - Word to the Wise
Expert view

Expert from Email Geeks shares that timeout errors with iCloud often occur when their infrastructure is overwhelmed, suggesting that ESPs can easily exceed their capacity.

January 2024 - Email Geeks
Expert view

Expert from Spam Resource shares that incorrect network configurations, particularly related to Maximum Transmission Unit (MTU) size, can result in timeout errors. They advise checking and adjusting MTU settings on your server to ensure they are compatible with iCloud's network requirements.

June 2024 - Spam Resource

What the documentation says
5Technical articles

iCloud email timeout errors can be attributed to various factors including temporary iCloud server issues, DNS resolution problems, general SMTP timeout errors due to network congestion or server overload, network problems revealed by checking email hop counts, and mail loop issues arising from incorrect forwarding rules or mail configurations. Documentation suggests monitoring system status, verifying DNS configurations, understanding SMTP protocols, investigating network paths, and checking for mail loop configurations.

Key findings

  • iCloud Server Issues: iCloud Mail may experience temporary server issues leading to timeouts.
  • DNS Resolution: Timeout errors can indicate DNS resolution problems with your domain.
  • SMTP Timeouts: SMTP timeout errors occur when a server doesn't receive a response within a specified time, often due to network congestion or server overload.
  • Network Problems: Timeout issues are commonly caused by underlying network problems.
  • Mail Loop Issues: NDR errors and timeout issues can be a result of incorrect forwarding rules or mail configurations causing mail loops.

Key considerations

  • Check Apple System Status: Regularly monitor the Apple System Status page for reported iCloud Mail outages.
  • Verify DNS Records: Use DNS lookup tools to ensure your domain's DNS records are correctly configured.
  • Understand SMTP Protocols: Familiarize yourself with SMTP timeout errors and potential causes such as network congestion.
  • Check Email Hop Counts: Check the hops an email takes, to reveal long delays.
  • Check Configuration: Review forwarding rules and mail configurations to avoid mail loops.
Technical article

Documentation from MXToolbox suggests that timeout errors can indicate DNS resolution problems. They advise using their DNS lookup tools to verify that your domain's DNS records are correctly configured and resolving properly.

April 2024 - MXToolbox
Technical article

Documentation from Apple Support explains that iCloud Mail might experience temporary server issues, causing timeouts. They recommend checking the Apple System Status page for any reported outages or maintenance. If there are no reported issues, they suggest trying again later.

April 2023 - Apple Support
Technical article

Documentation from AWS SES says that timeout issues are usually caused by network problems, and encourages checking the amount of hops an email takes to check for long delays, and also to retry the message later.

July 2023 - Amazon Web Services
Technical article

Documentation from Microsoft says that NDR errors can be caused by mail loop issues. They suggest checking your forwarding rules and mail configurations for configuration errors, to stop these looping messages being sent over and over.

February 2025 - Microsoft
Technical article

Documentation from RFC 5321 (Simple Mail Transfer Protocol) explains that SMTP timeout errors occur when a server doesn't receive a response from another server within a specified time. It suggests that network congestion or server overload can cause these timeouts.

January 2023 - RFC Editor