{"id":25290,"date":"2025-06-30T00:00:00","date_gmt":"2025-06-30T00:00:00","guid":{"rendered":"https:\/\/www.mailgun.com\/blog\/rechazo-dkim-outlook\/"},"modified":"2026-09-22T13:34:10","modified_gmt":"2026-09-22T13:34:10","slug":"rechazo-dkim-outlook","status":"publish","type":"blog","link":"https:\/\/www.mailgun.com\/es\/blog\/deliverability\/rechazo-dkim-outlook\/","title":{"rendered":"\u00bfPasa el DKIM, pero hay rebote de todos modos? El nuevo y misterioso rechazo de Outlook"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\">Word is coming in that Outlook is bouncing authenticated emails, and the \u2018why\u2019 is a bit of a mystery. Here\u2019s our take after diving into the logs, reports, and talking the ears of our industry peers.<\/p>\n\n<h2 class=\"wp-block-heading\">The backstory<\/h2>\n\n<p class=\"wp-block-paragraph\">In March 2025, Microsoft announced new sender requirements for Outlook, Hotmail, and Live.com inboxes. This is in line with new sender requirements that we saw Gmail and Yahoo release in 2024. We <i>immediately<\/i> covered Microsoft\u2019s changes on our <a href=\"https:\/\/www.mailgun.com\/es\/blog\/deliverability\/requisitos-remitentes-microsoft\/\" target=\"_tabs\" rel=\"noopener noreferrer\">blog<\/a>, and made them the focus of the second episode of <a href=\"https:\/\/www.mailgun.com\/es\/blog\/email\/resumen-episodio-dos-deliverability-academy\/\" target=\"_tabs\" rel=\"noopener noreferrer\">Deliverability Academy<\/a>.As seasoned deliverability veterans, we were prepared for some growing pains, and we expected that some senders might start seeing rejections due to stricter authentication requirements, but this error feels unexpected to senders. Here\u2019s our take.<\/p>\n\r\n    <nav data-content-type=\"longform\" class=\"toc-block longform-spacings px-5 py-6 px-md-6 px-lg-7 py-md-7 bg-light fs-sm rounded-lg\" aria-labelledby=\"toc-title-4489\"><p class=\"h5 m-0\" id=\"toc-title-4489\">\u00cdndice<\/p><div class=\"d-flex mt-3\"><div class=\"w-auto fw-bold text-accent d-flex me-2\">01<\/div><div class=\"d-flex flex-column\"><a class=\"fw-bold scrollme link-body-color text-accent\" href=\"#the-backstory\">The backstory<\/a><\/div><\/div><div class=\"d-flex mt-3\"><div class=\"w-auto fw-bold text-accent d-flex me-2\">02<\/div><div class=\"d-flex flex-column\"><a class=\"fw-bold scrollme link-body-color text-accent\" href=\"#a-deliverability-curveball-from-microsoft-and-what-you-can-do-about-it\">A deliverability curveball from Microsoft, and what you can do about it<\/a><\/div><\/div><div class=\"d-flex mt-3\"><div class=\"w-auto fw-bold text-accent d-flex me-2\">03<\/div><div class=\"d-flex flex-column\"><a class=\"fw-bold scrollme link-body-color text-accent\" href=\"#what-we-think-is-going-on-and-what-you-can-do-about-it\">What we think is going on and what you can do about it<\/a><a class=\"scrollme link-body-color\" href=\"#inconsistent-message-behavior\">Inconsistent message behavior<\/a><a class=\"scrollme link-body-color\" href=\"#suspected-false-dkim-failures\">Suspected false DKIM failures<\/a><a class=\"scrollme link-body-color\" href=\"#content-sensitivity\">Content sensitivity<\/a><a class=\"scrollme link-body-color\" href=\"#key-age\">Key age<\/a><a class=\"scrollme link-body-color\" href=\"#header-inconsistencies\">Header inconsistencies<\/a><a class=\"scrollme link-body-color\" href=\"#volume-trends\">Volume trends<\/a><\/div><\/div><div class=\"d-flex mt-3\"><div class=\"w-auto fw-bold text-accent d-flex me-2\">04<\/div><div class=\"d-flex flex-column\"><a class=\"fw-bold scrollme link-body-color text-accent\" href=\"#faq-for-all-senders\">FAQ For all senders<\/a><a class=\"scrollme link-body-color\" href=\"#how-do-you-keep-dkim-keys-fresh\">How do you keep DKIM keys fresh?<\/a><a class=\"scrollme link-body-color\" href=\"#when-should-i-check-alignment\">When should I check alignment?<\/a><a class=\"scrollme link-body-color\" href=\"#how-should-i-simplify-headers\">How should I simplify headers?<\/a><a class=\"scrollme link-body-color\" href=\"#how-should-i-monitor-deliverability\">How should I monitor deliverability?<\/a><\/div><\/div><div class=\"d-flex mt-3\"><div class=\"w-auto fw-bold text-accent d-flex me-2\">05<\/div><div class=\"d-flex flex-column\"><a class=\"fw-bold scrollme link-body-color text-accent\" href=\"#faq-for-esps-and-high-volume-senders\">FAQ For ESPs and High-Volume Senders<\/a><a class=\"scrollme link-body-color\" href=\"#what-do-i-need-to-understand-dual-dkim-behavior\">What do I need to understand dual DKIM behavior<\/a><\/div><\/div><div class=\"d-flex mt-3\"><div class=\"w-auto fw-bold text-accent d-flex me-2\">06<\/div><div class=\"d-flex flex-column\"><a class=\"fw-bold scrollme link-body-color text-accent\" href=\"#wrapping-up-what-mailgun-is-doing\">Wrapping up: What Mailgun is doing<\/a><\/div><\/div><div class=\"d-flex mt-3\"><div class=\"w-auto fw-bold text-accent d-flex me-2\">07<\/div><div class=\"d-flex flex-column\"><a class=\"fw-bold scrollme link-body-color text-accent\" href=\"#the-bottom-line\">The Bottom line<\/a><\/div><\/div><\/nav>\n<h2 class=\"wp-block-heading\">A deliverability curveball from Microsoft, and what you can do about it<\/h2>\n\n<p class=\"wp-block-paragraph\">Over the past few weeks, a rising number of Mailgun customers (and industry peers across other ESPs) have encountered bounce messages like this:<\/p>\n\n<p class=\"wp-block-paragraph\"><code>550 5.7.515 Access denied, sending domain DOMAIN.TLD doesn't meet the required authentication level. The sender's domain in the 5322.From address doesn't meet the authentication requirements defined for the sender. <\/code><\/p>\n\n<p class=\"wp-block-paragraph\">These errors often show:<\/p>\n\n<ul class=\"wp-block-list\">\n<li>SPF = Pass<\/li>\n\n\n\n<li>DKIM = Fail (but falsely!)<\/li>\n\n\n\n<li>DMARC = Pass<\/li>\n<\/ul>\n\n<p class=\"wp-block-paragraph\">In short:<b> DKIM appears to pass in one place (like Gmail or your DMARC reports) but fails at Microsoft. <\/b>And when it fails, Outlook blocks the message, even if it meets standard DMARC policy of p=none.<\/p>\n\n<h2 class=\"wp-block-heading\">What we think is going on and what you can do about it<\/h2>\n\n<p class=\"wp-block-paragraph\">We don\u2019t have a complete answer yet, but here\u2019s what we\u2019ve learned so far, both from our own data and broader industry collaboration:<\/p>\n\n<h3 class=\"wp-block-heading\">Inconsistent message behavior<\/h3>\n\n<p class=\"wp-block-paragraph\">Some <a href=\"https:\/\/www.mailgun.com\/es\/blog\/deliverability\/rebotes-email-que-hacer-al-respecto\/\" target=\"_tabs\" rel=\"noopener noreferrer\">messages bounce<\/a>; others don\u2019t, even with identical headers and content. Previously unaffected domains might suddenly start failing.<\/p>\n\n<h4 class=\"wp-block-heading\">If you\u2019re seeing 550 5.7.515 errors start by confirming your authentication setup<\/h4>\n\n<ul class=\"wp-block-list\">\n<li>SPF: Must include Mailgun IPs and stay under the 10-lookup limit.<\/li>\n\n\n\n<li>DKIM: Check that your DKIM TXT record is correctly published in DNS (preferably as a single-line value) and matches the selector used by Mailgun for signing.<\/li>\n\n\n\n<li>DMARC: Valid policy (p=none\/quarantine\/reject) aligned with SPF or DKIM.<\/li>\n<\/ul>\n\n<h3 class=\"wp-block-heading\">Suspected false DKIM failures<\/h3>\n\n<p class=\"wp-block-paragraph\">Messages pass <a href=\"https:\/\/www.mailgun.com\/es\/blog\/deliverability\/entender-dkim-como-funciona\/\" target=\"_tabs\" rel=\"noopener noreferrer\">DKIM<\/a> at Gmail and Yahoo but fail at Microsoft. Our working theory is that Microsoft is applying additional checks prior to delivery (breaking DKIM) or interpreting alignment more strictly than DMARC requires.<\/p>\n\n<h4 class=\"wp-block-heading\">How to fix: Check alignment<\/h4>\n\n<ul class=\"wp-block-list\">\n<li>Microsoft may be enforcing <b>strict alignment<\/b>, even if <a href=\"https:\/\/www.mailgun.com\/es\/blog\/deliverability\/implementar-dmarc\/\" target=\"_tabs\" rel=\"noopener noreferrer\">DMARC<\/a> allows relaxed.<\/li>\n\n\n\n<li>If you\u2019re seeing persistent bounces, contact our support team to explore signing directly with your root domain (e.g., example.com). While Mailgun typically uses a subdomain for DKIM, strict alignment with the From domain may improve deliverability to Microsoft.<\/li>\n<\/ul>\n\n<h3 class=\"wp-block-heading\">Content sensitivity<\/h3>\n\n<p class=\"wp-block-paragraph\">Emails with these factors seem more likely to be rejected:<\/p>\n\n<ul class=\"wp-block-list\">\n<li>Non-ASCII characters (like accents or emojis)<\/li>\n\n\n\n<li>MIME-encoded headers (Subject or From)<\/li>\n<\/ul>\n\n<h3 class=\"wp-block-heading\">Key age<\/h3>\n\n<p class=\"wp-block-paragraph\">Older <a href=\"https:\/\/www.mailgun.com\/es\/blog\/deliverability\/entender-dkim-como-funciona\/\" target=\"_tabs\" rel=\"noopener noreferrer\">DKIM keys,<\/a> especially those last rotated before March 2025, seem more vulnerable. Newer keys show fewer failures.<\/p>\n\n<h4 class=\"wp-block-heading\">How to fix: Consider DKIM key rotation<\/h4>\n\n<p class=\"wp-block-paragraph\">Even the strongest keys have a shelf life. If a DKIM key gets exposed, it can open the door to spoofing, spam, and replay attacks that piggyback off your good reputation. That&#8217;s bad news for your brand, and for anyone else sending from the same IP.<\/p>\n\n<p class=\"wp-block-paragraph\">To reduce the risk, it\u2019s best practice to <a href=\"https:\/\/help.mailgun.com\/hc\/en-us\/articles\/16956951504539-How-can-I-rotate-my-DKIM-key\" target=\"_tabs\" rel=\"noopener noreferrer\">rotate your DKIM keys<\/a> every 6\u201312 months. If you\u2019re using Mailgun\u2019s Automatic Sender Security, congrats! We\u2019ve got this covered. But if you manage your own DNS or use a custom sending domain, it\u2019s up to you to schedule regular key updates.<\/p>\n\n<ul class=\"wp-block-list\">\n<li>Consider rotating any DKIM keys older than 6\u201312 months.<\/li>\n\n\n\n<li>Wait for DNS to propagate, then retest.<\/li>\n<\/ul>\n\n<h3 class=\"wp-block-heading\">Header inconsistencies<\/h3>\n\n<p class=\"wp-block-paragraph\">If a DKIM signature references headers that are missing from the actual message (e.g., MessageID:), it can invalidate the signature. <\/p>\n\n<h4 class=\"wp-block-heading\">How to fix: Look at the headers you can access<\/h4>\n\n<p class=\"wp-block-paragraph\">You won\u2019t be able to view full headers from a message that Microsoft rejects, but you can still get clues elsewhere. Review the headers of a successfully delivered message from a different provider to spot potential header or encoding issues like:<\/p>\n\n<ul class=\"wp-block-list\">\n<li>Non-ASCII characters (like emojis or accents) in Subject or From<\/li>\n\n\n\n<li>MIME encoding that might be interpreted differently by Outlook<\/li>\n\n\n\n<li>Which headers were signed via DKIM vs. which ones were actually included in the message<\/li>\n\n\n\n<li>Differences in DKIM signature alignment (e.g., subdomain vs. root domain)<\/li>\n<\/ul>\n    <div data-content-type=\"longform\"  class=\"callout text-body-color px-5 py-6 px-md-6 px-lg-7 py-md-7 longform-spacings rounded-lg bg-light\" data-theme=\"light\">\r\n\r\n        <div class=\"content-body\"> Use a test seed list that includes both Gmail and Outlook addresses, so you can monitor what gets through vs. what bounces. Need help interpreting headers? <a href=\"https:\/\/mxtoolbox.com\/EmailHeaders.aspx\">MXToolbox<\/a> and other parsing tools are great places to start.<\/div>\r\n    <\/div>\r\n\n<h3 class=\"wp-block-heading\">Volume trends<\/h3>\n\n<p class=\"wp-block-paragraph\">Roughly 1.8% of Microsoft-related bounces in our data from May\u2013June 2025 stem from authentication issues \u2013 mostly Hotmail. High-volume senders may be more exposed, either due to message complexity or just scale.<\/p>\n\n<h4 class=\"wp-block-heading\">How to fix: Make sure you\u2019re monitoring your authentication<\/h4>\n\n<p class=\"wp-block-paragraph\">Use DMARC Reports like <a href=\"https:\/\/www.mailgun.com\/es\/blog\/product\/asociacion-mailgun-redsift\/\" target=\"_tabs\" rel=\"noopener noreferrer\">Red Sift<\/a> or similar tools to see where failures are happening, and what IPs\/domains are affected and review the sender guidelines in detail. Gmail and Yahoo have very specific thresholds but Microsoft&#8217;s approach reminds us that Inbox providers are looking at several behavioral factors, not just technical ones.<\/p>\n\n<h2 class=\"wp-block-heading\">FAQ For all senders<\/h2>\n\n<h3 class=\"wp-block-heading\">How do you keep DKIM keys fresh?<\/h3>\n\n<p class=\"wp-block-paragraph\">Since regular key rotation is a best practice, give yours a quick review. If you <a href=\"https:\/\/help.mailgun.com\/hc\/en-us\/articles\/16956951504539-How-can-I-rotate-my-DKIM-key\" target=\"_tabs\" rel=\"noopener noreferrer\">rotate manually<\/a> and your current key predates May 2025, it may be time for a refresh. Even valid keys can be rejected if Microsoft is filtering based on adherence to best practices; a new one may help alleviate these false failures.<\/p>\n\n<h3 class=\"wp-block-heading\">When should I check alignment?<\/h3>\n\n<p class=\"wp-block-paragraph\">Microsoft may be applying stricter alignment logic than DMARC requires, and not always in predictable ways. Even if you\u2019re signing with your <i>root domain<\/i> and using a subdomain in your From: address (or vice versa), rejections may still occur.<\/p>\n\n<p class=\"wp-block-paragraph\">It\u2019s a good idea to check alignment, but don\u2019t assume simpler is better. If you&#8217;re unsure whether your current DKIM setup is strict or relaxed, or want to explore adjustments, our support team can help review your domain configuration.<\/p>\n\n<h3 class=\"wp-block-heading\">How should I simplify headers?<\/h3>\n\n<p class=\"wp-block-paragraph\">Avoid emojis, accented characters, or unnecessarily complex MIME-encoding in your From: or Subject: fields. If you\u2019re troubleshooting rejections, test with a stripped-down message to rule out encoding-related surprises.<\/p>\n\n<h3 class=\"wp-block-heading\">How should I monitor deliverability?<\/h3>\n\n<p class=\"wp-block-paragraph\">Use DMARC aggregate reports (via tools like <a href=\"https:\/\/www.mailgun.com\/es\/blog\/product\/asociacion-mailgun-redsift\/\" target=\"_tabs\" rel=\"noopener noreferrer\">Red Sift<\/a>) to keep an eye on alignment issues, unauthorized senders, and shifting bounce trends\u2014especially at Outlook, Hotmail, and Live domains.<\/p>\n\n<h2 class=\"wp-block-heading\">FAQ For ESPs and High-Volume Senders<\/h2>\n\n<h3 class=\"wp-block-heading\">What do I need to understand dual DKIM behavior<\/h3>\n\n<p class=\"wp-block-paragraph\">Mailgun already dual-signs messages for many customers, typically using both a platform domain and the customer\u2019s subdomain. In theory, this should meet the highest standard for authentication. However, based on industry chatter and what we\u2019ve seen, Microsoft may be evaluating only one of the signatures (and not always the one that passes alignment).<\/p>\n\n<p class=\"wp-block-paragraph\">We\u2019re actively researching whether Microsoft is misapplying DKIM evaluation logic in dual-signed messages, and if so, what patterns or configurations increase risk.<\/p>\n\n<h4 class=\"wp-block-heading\">What should my domain structure look like?<\/h4>\n\n<p class=\"wp-block-paragraph\">Avoid unnecessarily complex subdomain configurations (e.g., send13.mailgun.example.com) unless critical to your setup. Overly specific or inconsistent subdomains may increase the chance of alignment confusion or DNS resolution hiccups.<\/p>\n\n<h4 class=\"wp-block-heading\">What do my clients need to know?<\/h4>\n\n<p class=\"wp-block-paragraph\">If you&#8217;re an ESP or agency working on behalf of senders, help your customers:<\/p>\n\n<ul class=\"wp-block-list\">\n<li>Understand DKIM alignment<\/li>\n\n\n\n<li>Avoid risky content and headers<\/li>\n\n\n\n<li>Regularly review DNS and rotate keys<\/li>\n<\/ul>\n\n<h2 class=\"wp-block-heading\">Wrapping up: What Mailgun is doing<\/h2>\n\n<p class=\"wp-block-paragraph\">We\u2019re not just watching, we\u2019re working:<\/p>\n\n<ul class=\"wp-block-list\">\n<li><b>Ongoing Monitoring:<\/b> We&#8217;re tracking bounce trends across all Microsoft-bound traffic.<\/li>\n\n\n\n<li><b>Industry Collaboration:<\/b> We\u2019re talking with other ESPs and providers to pool insights and build pressure for Microsoft transparency.<\/li>\n\n\n\n<li><b>Customer Support:<\/b> We\u2019re helping users audit their settings and run tests.<\/li>\n\n\n\n<li><b>Escalation:<\/b> We\u2019re compiling data to present to Microsoft and pushing for clarity on these false DKIM failures.<\/li>\n<\/ul>\n\n<p class=\"wp-block-paragraph\">Unfortunately, there\u2019s no guaranteed workaround yet. But here&#8217;s what seems to help reduce bounce rates:<\/p>\n\n<ul class=\"wp-block-list\">\n<li>Freshly rotated DKIM keys<\/li>\n\n\n\n<li>Simpler headers with ASCII-only characters<\/li>\n\n\n\n<li>Fewer MIME-encoded fields in From: and Subject:<\/li>\n<\/ul>\n\n<p class=\"wp-block-paragraph\">We\u2019re closely monitoring all of the above to determine which changes consistently make a difference.<\/p>\n\n<h2 class=\"wp-block-heading\">The Bottom line<\/h2>\n\n<p class=\"wp-block-paragraph\">This issue isn\u2019t limited to Mailgun, or even to ESPs in general, it\u2019s a broader issue stemming from Microsofts evolving filtering behaviors. We\u2019re in the thick of it with the rest of the industry, and we\u2019ll continue to share what we learn.<\/p>\n\n<p class=\"wp-block-paragraph\">If you\u2019re a Mailgun customer and need help troubleshooting 550 5.7.515 errors, <a href=\"mailto:support@mailgun.com\" target=\"_tabs\" rel=\"noopener noreferrer\">reach out to our Support team<\/a> with as much detail as possible: affected domains, bounce messages, and full headers.<\/p>\n\n<p class=\"wp-block-paragraph\">We\u2019ll update this post as the situation evolves. Stay tuned and stay authenticated.<\/p>\n\r\n    <aside data-content-type=\"longform\"  class=\"banner-block longform-spacings rounded-lg shadow-lg px-5 py-6 px-md-6 py-md-7 p-lg-7 bg-light\" data-theme=\"dark\" aria-labelledby=\"banner-block-block_00e5978c50f1283713803f8e0cf3f8c1\">\r\n                    <p class=\"text-uppercase section-caption text-body-color\">\r\n                Sign Up            <\/p>\r\n                            <p class=\"h4 text-accent fw-bold\" id=\"banner-block-block_00e5978c50f1283713803f8e0cf3f8c1\">\r\n                It&#x27;s easy to get started. And it&#x27;s free.            <\/p>\r\n                            <div class=\"mb-0 text-body-color\">\r\n                                    <div class=\"content-body mb-0 text-body-color\">See what you can accomplish with the world\u2019s best email delivery platform.<\/div>\r\n                            <\/div>\r\n        \r\n        <div class=\"text-start mt-5\"><a href=\"https:\/\/signup.mailgun.com\/new\/signup\"  class=\"btn btn-secondary\" >Get Started<\/a><\/div>\r\n    <\/aside>\r\n\r\n","protected":false},"excerpt":{"rendered":"<p>Hemos recibido informes sobre el rechazo de emails autenticados por parte de Outlook, incluso cuando DMARC indica un aprobado. Hemos revisado los registros, hablado con colegas y profundizado en el problema. Esto es lo que sabemos y lo que puedes hacer.<\/p>\n","protected":false},"author":89,"featured_media":4376,"menu_order":0,"template":"","meta":{"_acf_changed":false,"footnotes":""},"blog_category":[21],"class_list":["post-25290","blog","type-blog","status-publish","has-post-thumbnail","hentry","blog_category-deliverability"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v28.4 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>\u00bfOutlook rebota los emails con DKIM validado? Esto es lo que necesitas saber | Mailgun<\/title>\n<meta name=\"description\" content=\"Outlook est\u00e1 rebotando emails autenticados incluso con claves DKIM v\u00e1lidas. 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