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Known Issue: Email Delivery Disruptions to Microsoft Domains

Marketing

Issue Number: 3481229

Issue Status: Support Researching

Date Reported:
04/22/2025

Estimated Resolution Date: 5/13/2025

Summary:
12/22/2025 -- 12:00 PM The global issue affecting email delivery to Microsoft domains was resolved in mid-November. We kept this open as a precaution, as similar issues have resurfaced in past years—particularly around the Thanksgiving weekend. Currently, we’re not seeing any global blocks across the network. However, some senders are still experiencing isolated bounces with similar error messages. These are now tied to individual sender reputation rather than a system-wide problem. With recent improvements to email header alignment and return-path configurations, Microsoft has better visibility into who is sending the mail. They are now tracking reputation on a per-sender basis. If you're still seeing bounces, it's often due to one or more of the following: Sending high volumes of unengaged mail Hitting spam traps A spike in spam complaints from Microsoft recipients We recommend reviewing and adjusting your sending practices to improve engagement and reduce risk of future delivery issues. 08/13/2025 – 10:00 AM In the past week, we’ve seen encouraging progress with Microsoft’s handling of our mail. More messages are being accepted, and the volume of permanent (hard) bounces has decreased. In many cases, Microsoft is now issuing temporary (soft) bounces with rate-limit responses, which typically deliver on retry. While these improvements are promising, individual users may still see similar levels of impact if their sending practices are not fully compliant. Microsoft’s filtering remains strict, but it has stabilized and become more consistent. We continue to see higher filtering on high-risk IP groups, with some spillover to lower-risk IPs—especially those sharing reputation space with higher-risk senders. This collateral impact is decreasing but not yet resolved. Microsoft maintains a zero-tolerance policy toward violations, and their enforcement reflects this stance. Ongoing Root Causes Key factors contributing to these deliverability challenges include: -Sending to invalid or outdated addresses -Triggering spam traps -Generating high complaint rates -Sending large volumes to unengaged contacts (most significant) These behaviors damage overall sending reputation and now affect even historically lower-risk traffic. Our Remediation Efforts To improve deliverability, we are implementing restrictions on sending to unengaged contacts. Beginning in mid to late August, any contact without engagement in the past 18+ months will no longer be sent email from the Keap email Network. More details and timelines will be sent via email in the coming weeks. We appreciate your continued commitment to sending best practices and supporting our work to restore full deliverability with Microsoft. If you have questions or need help with engagement strategies or compliance, please reach out to our team. 07/08/2025 9:00AM Microsoft continues to strictly enforce its updated sending requirements, which officially took effect on May 5, 2025—though we began seeing enforcement as early as February. While we initially made meaningful progress with improved acceptance rates across the Keap network, a recent, unrelated issue led to a significant spike in unsolicited mail targeting Microsoft users. This setback impacted our overall network reputation and delayed further progress. Currently, Microsoft’s filtering behavior remains volatile—changing by the hour—and users may experience varying levels of impact based on their individual sender reputation. While the most severe filtering continues to occur on high-risk IP groups, we’re also seeing collateral impact on lower-risk IPs, especially those adjacent to or sharing reputation space with higher-risk senders. Microsoft is holding a zero-tolerance stance on policy violations, and their enforcement reflects this posture. Root Causes of Ongoing Issues The key drivers behind these deliverability challenges continue to be: -Sending to invalid or outdated email addresses -Hitting spam traps -Generating high complaint rates -Most significantly, sending large volumes to unengaged contacts These behaviors degrade our overall sending reputation and are now affecting even traditionally lower-risk traffic. What We’re Doing We are actively investigating and addressing these issues across the network. As part of our remediation efforts, we are implementing new safeguards to limit sending to unengaged contacts beyond a defined period of inactivity. More details and timelines on this change will be communicated via email in the coming weeks. We appreciate your continued efforts to follow sending best practices and support our work in restoring full deliverability with Microsoft. Please don’t hesitate to reach out if you have questions or need guidance on engagement strategies or compliance. 05/14/2025 8:30AM We are continuing to experience delivery issues across the network. Late yesterday, Microsoft provided some relief for low-risk IPs; however, they are not granting any leniency for high-risk IPs(121+ days with no engagement contacts). Below is their response to our delisting request: "These IP(s) have previously received mitigations from deliverability support, and have failed to maintain patterns within our guidelines, so they are ineligible for additional mitigation at this time. Please note: This outcome indicates behavior that misses standards" Microsoft is maintaining a strict stance, with near-zero tolerance for any infractions. This approach aligns with the updated requirements that officially took effect on May 5, 2025, though we began seeing signs of enforcement earlier. The primary root causes of these issues include: -Sending to invalid email addresses -Hitting spam traps -Generating abuse complaints -Most significantly, sending high volumes of email to unengaged contacts These ongoing poor practices have carried over and are contributing to sending issues even on the lower-risk IP ranges. We are continuing to investigate and address these issues to improve deliverability. 04/30/2025 12:45PM Last week and over the weekend, Microsoft granted us a temporary reprieve for IPs within the low-risk pools. As a result, we've seen a significant drop in bounce rates—down to nearly zero—except for isolated cases involving users who are not following email best practices. However, we're still experiencing notable delivery issues across the high-risk IP ranges. These issues primarily affect mail sent to contacts who have not engaged in 121+ days, as well as to leads who have never interacted with any emails during their time in a user’s app. While Microsoft did reduce bounce rates across these high-risk groups over the weekend, the current levels may shift following the big sending volume days of the start of the week—Tuesday being our highest-volume day. We continue to address the root causes on our side. These include: -Excessive spam/abuse reports from Microsoft recipients, -High volumes of mail sent to invalid or deactivated addresses, -Large-scale sends to unengaged users, -And mail hitting Microsoft-managed spam traps. We are proactively identifying the worst offending users in these areas and requiring them to undergo a thorough review and overhaul of their sending practices. This includes improvements in list management, content relevance, opt-in transparency, and overall adherence to email compliance standards. As we take corrective action across more users, we’re seeing gradual improvements and incremental IP delistings from Microsoft. While we still have work to do, we are seeing early signs that our efforts are having a positive impact. We will continue to share updates as we gather more data and monitor progress. 04/22/2025 We are currently experiencing delivery challenges affecting emails sent to Microsoft-hosted domains (including @hotmail.com, @outlook.com, @live.com, and @msn.com) from several of our shared IP addresses. Impacted messages are being blocked by Microsoft’s filtering systems, resulting in permanent delivery failures (hard bounces). Issue Summary The majority of these delivery blocks are occurring on our high-risk IP addresses. These IPs typically serve senders who are mailing to unengaged recipients—those who have not interacted with messages in over 120 days. The primary driver of the IP reputation issues is mail sent to unengaged users that are either: - Reporting the messages as spam or abusive, or - Associated with spam traps. We are also observing similar, though less severe, delivery issues on some lower-risk IPs. Current Status We are actively engaging with Microsoft to address this issue. However, their diagnostic feedback does not currently align with the data observed on our end, and discussions are ongoing to reconcile these discrepancies. A temporary improvement in deliverability was noted on April 17 and 18, but the issue has since reverted to previous levels. In the meantime, we are implementing enhanced monitoring across the network and proactively flagging accounts that: - Generate high volumes of bounces, - Receive excessive abuse complaints, or - Trigger spam trap hits. Accounts identified with problematic sending behaviors—particularly toward Microsoft domains—are being required to take immediate remedial action. How to Identify Affected Emails Hard bounces related to this issue may include error responses such as: 550 5.7.1 Unfortunately, messages from [35.227.130.???] weren't sent. Please contact your Internet service provider since part of their network is on our block list (S3140). You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors. [Name=Protocol Filter Agent][AGT=PFA][MxId=11BAFDC738C11B14] [CY4PEPF0000E9D3.namprd03.prod.outlook.com 2025-04-22T03:26:01.277Z 08DD7EE39EE752BC] What You Can Do Improving email deliverability across the network requires the collective effort of all senders. Please review your sending practices to ensure optimal list hygiene and recipient engagement. Specifically: - Send only to active and engaged contacts. Avoid mailing users who have not opened or clicked in the past 90–120 days. Maintain clean lists. Regularly remove inactive or bounced addresses. Industry standards suggest that 25% of email contacts become inactive each year. - Audit your opt-in process. Set clear expectations at the point of signup regarding: - - Who the emails will be from - - The nature of the content - - How frequently messages will be sent - - The value subscribers can expect - Honor opt-in expectations. Consistency between your stated practices and actual sending behavior builds trust and improves long-term engagement. We will continue to closely monitor this situation and provide updates as new information becomes available. Thank you for your cooperation and commitment to responsible email sending.

Product Line: Keap Pro/Max

Classic/Ultimate - Some Apps: Checking out via Order Forms results in the error message "There was a problem validating your checkout session. Order placement is cancelled. Please start over and place your order again"

E-Commerce

Issue Number: 3544219

Date Reported:
12/04/2025

Summary:
We have received reports that some applications are having contacts encounter the error "There was a problem validating your checkout session. Order placement is cancelled. Please start over and place your order again" when they try and check out via Order Forms. We are currently investigating these reports.

Alternative Solution:
Currently, if users are experiencing this they need to contact Customer Support and an ASR will need to turn OFF the fs.61290.session.jwt.orderForms feature flag for their application.

Product Line: Keap Pro/Max

List Box custom fields now return the invisible "carriage return" (/r/n, or &#013) character as part of the value

CRM

Issue Number: 3545734

Issue Status: Deployed

Date Reported:
12/11/2025

Estimated Resolution Date: 12/11/2025

Summary:
December 12th 2025 12:04 PM MST We've decided to re-prioritize this issue and are planning to have it corrected today. December 11th 2025 4:40 PM MST Our developmebt team has created a fix and is discussing how quickly this can be implemented in customer apps. December 11th 2025 9:51 AM MST We have confirmed the cause of this issue as being associated with a recent update which started on December 9th 2025 at approximately 7:30 PM MST. December 11th 2025 9:32 AM MST When retrieving contact custom fields of the "List Box" type, carriage returns intended to act as a delimiter between separate selectable values are now being included as if they are part of the value for the custom field. This affects not only how API calls must process retrieved information, but prevents in-app searches, exports, and saving records based on these values from functioning as intended.

Alternative Solution:
None

Product Line: Keap Pro/Max

Country selection is not functional in all order placing or payment capture processes.

E-Commerce

Issue Number: 3546046

Issue Status: Deployed

Date Reported:
12/12/2025

Estimated Resolution Date: 1/23/2026

Summary:
12/12/25 12:37PM MST Code fix is complete. deploying code fix to all apps. 12/12/25 11:38AM MST Identified that via checkout forms, and Manual recorded payments the country field dropdown is not retaining the selection. This can be seen by users or contacts if looking at one of these options. This is a Pro/Max/Ultimate affecting.

Product Line: Keap Pro/Max

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Urgent 3 days
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