{"id":33724,"date":"2021-09-24T16:49:55","date_gmt":"2021-09-24T20:49:55","guid":{"rendered":"https:\/\/mjtsai.com\/blog\/?p=33724"},"modified":"2022-02-17T09:26:32","modified_gmt":"2022-02-17T14:26:32","slug":"some-web-sites-will-stop-working-with-el-capitan-and-older","status":"publish","type":"post","link":"https:\/\/mjtsai.com\/blog\/2021\/09\/24\/some-web-sites-will-stop-working-with-el-capitan-and-older\/","title":{"rendered":"Some Web Sites Will Stop Working With El Capitan and Older"},"content":{"rendered":"<p><a href=\"https:\/\/scotthelme.co.uk\/lets-encrypt-old-root-expiration\/\">Scott Helme<\/a> (<a href=\"https:\/\/news.ycombinator.com\/item?id=28596317\">Hacker News<\/a>):<\/p>\n<blockquote cite=\"https:\/\/scotthelme.co.uk\/lets-encrypt-old-root-expiration\/\"><p>On 30th September 2021, the root certificate that Let&rsquo;s Encrypt are currently using, the IdentTrust DST Root CA X3 certificate, will expire. You may or may not need to do anything about this Root CA expiring, but I&rsquo;m betting a few things will probably break on that day so here&rsquo;s what you need to know!<\/p><p>[&#8230;]<\/p><p>In normal circumstances this event, a root CA expiring, wouldn&rsquo;t even be worth talking about because the transition from an old root certificate to a new root certificate is completely transparent. The reason we&rsquo;re having a problem at all is because clients don&rsquo;t get updated regularly and if the client doesn&rsquo;t get updated, then the new root CA that replaces the old, expiring root CA is not downloaded onto the device.<\/p><p>[&#8230;]<\/p><p>In the last year alone, Let&rsquo;s Encrypt have grown their market share quite a lot and as a CA becomes larger, it&rsquo;s certificates enable more of the Web to operate and as a result, when something like this comes along they have the potential to cause more problems. This is nothing to do with what Let&rsquo;s Encrypt have done, or have not done, this still comes down to the same underlying problem that devices out in the ecosystem aren&rsquo;t being updated as they should be.<\/p><p>[&#8230;]<\/p><p>Because old Android devices don&rsquo;t check the expiration date of a root certificate when they use it, Let&rsquo;s Encrypt may be able to continue to chain down to the expired root certificate without any problem on those older devices.<\/p><\/blockquote>\n\n<p><a href=\"https:\/\/eclecticlight.co\/2021\/09\/21\/el-capitan-and-older-mac-os-x-are-about-to-have-a-security-certificate-problem\/\">Howard Oakley<\/a>:<\/p>\n<blockquote cite=\"https:\/\/eclecticlight.co\/2021\/09\/21\/el-capitan-and-older-mac-os-x-are-about-to-have-a-security-certificate-problem\/\">\n<p>If you&rsquo;re still running El Capitan, or any version of Mac OS X prior to 10.12.1, then you&rsquo;re about to run into problems with some popular security certificates.<\/p>\n<\/blockquote>\n\n<p>macOS 10.11 was only superceded five years ago, and some older hardware can&rsquo;t run 10.12. On the iOS side, an iPhone 4S can&rsquo;t update to iOS 10. I get that Apple doesn&rsquo;t want to provide security bug fixes that far back, but how hard would it be to have a mechanism for updating the root certificates? (Then again, <a href=\"https:\/\/piunikaweb.com\/2021\/06\/15\/app-store-update-page-on-high-sierra-broken-as-per-some-mac-users\/\">even the Mac App Store<\/a> no longer works properly on macOS 10.13 due to a bad CSS URL.)<\/p>\n\n<p>Let&rsquo;s Encrypt is quite popular now, and there are other certificates issued using the same root. Lots of sites will break, and users won&rsquo;t know what to do.<\/p>\n\n<p>This blog and the <a href=\"https:\/\/forum.c-command.com\">C-Command forum<\/a> use Let&rsquo;s Encrypt, and they are set to redirect HTTP to HTTPS. I haven&rsquo;t decided how to handle this yet. So far, it seems like the only options are to accept the breakage or to buy a certificate from another provider.<\/p>\n\n<p>The main <a href=\"https:\/\/c-command.com\">C-Command site<\/a> (which my apps use for automatic software updates) uses a different certificate that should continue to work. One of the mirror download sites does use Let&rsquo;s Encrypt; if you get an error due do that you could try again until you get the non&#x2013;Let&rsquo;s Encrypt mirror.<\/p>\n\n<p>Previously:<\/p>\n<ul>\n<li><a href=\"https:\/\/mjtsai.com\/blog\/2018\/07\/25\/googles-http-not-secure-warning\/\">Google&rsquo;s HTTP &ldquo;Not Secure&rdquo; Warning<\/a><\/li>\n<li><a href=\"https:\/\/mjtsai.com\/blog\/2018\/02\/26\/google-and-http\/\">Google and HTTP<\/a><\/li>\n<li><a href=\"https:\/\/mjtsai.com\/blog\/2015\/05\/17\/the-rush-to-deprecate-http\/\">The Rush to &ldquo;Deprecate&rdquo; HTTP<\/a><\/li>\n<\/ul>\n\n<p id=\"some-web-sites-will-stop-working-with-el-capitan-and-older-update-2021-10-04\">Update (2021-10-04): <a href=\"https:\/\/mjtsai.com\/blog\/2021\/09\/24\/some-web-sites-will-stop-working-with-el-capitan-and-older\/#comment-3538503\">Commenter &ldquo;a&rdquo;<\/a> and <a href=\"https:\/\/www.arqbackup.com\/blog\/how-to-fix-error-1202-on-mac-os-x-prior-to-10-12-1\/\">Stefan Reitshamer<\/a> have posted instructions for how to download a new root certificate so that certificates from Let&rsquo;s Encrypt and others can still be trusted on macOS 10.11.<\/p>\n\n<p><a href=\"https:\/\/eclecticlight.co\/2021\/10\/01\/why-wont-safari-open-that-web-page\/\">Howard Oakley<\/a>:<\/p>\n<blockquote cite=\"https:\/\/eclecticlight.co\/2021\/10\/01\/why-wont-safari-open-that-web-page\/\"><p>A few days ago <a href=\"https:\/\/eclecticlight.co\/2021\/09\/21\/el-capitan-and-older-mac-os-x-are-about-to-have-a-security-certificate-problem\/\">I warned<\/a> that those still using older versions of Mac OS X are likely to have problems making secure HTTPS connections with many websites, because of a security certificate due to expire on 30 September. Unfortunately, it has turned out that this isn&rsquo;t confined to older Mac OS X, and can even affect Monterey betas. And there&rsquo;s more than one certificate which has now expired.<\/p><p>[&#8230;]<\/p><p>Although this is a <em>Let&rsquo;s Encrypt<\/em> certificate chain, the first of the certificates to expire wasn&rsquo;t its DST Root CA X3 which <a href=\"https:\/\/scotthelme.co.uk\/lets-encrypt-old-root-expiration\/\">we were warned about<\/a>, which remained valid at the time that this happened to me. The first certificate to expire was the intermediate R3, which expired on 29 September, a day earlier.<\/p><p>[&#8230;]<\/p><p>So how come two different Macs connecting to the same site get such different chains of trust?<\/p><p>The answer I suspect lies in the caching of certificate checks. Both my iMac and iPhone have connected to this site previously, and rather than performing a full certificate check every time, macOS is just using old results, which still refer to the old intermediate and Root certificates. My M1 Mac mini had never connected to that site, so had to perform a fresh check on the chain of trust, which then traced back to the current chain with its replaced intermediate and Root certificates.<\/p><\/blockquote>\n\n<p><a href=\"https:\/\/eclecticlight.co\/2021\/10\/02\/explainer-security-certificates\/\">Howard Oakley<\/a>:<\/p>\n<blockquote cite=\"https:\/\/eclecticlight.co\/2021\/10\/02\/explainer-security-certificates\/\"><p>In the rest of this article, I&rsquo;ll focus on the use of security certificates for one of their most common purposes, in establishing a secure connection to a remote server using the HTTPS protocol, using Transport Layer Security (TLS), which long ago was known as the Secure Sockets Layer (SSL) and is still occasionally referred to incorrectly as being SSL.<\/p><\/blockquote>\n\n<p><a href=\"https:\/\/eclecticlight.co\/2021\/10\/03\/last-week-on-my-mac-web-woes-worsen\/\">Howard Oakley<\/a>:<\/p>\n<blockquote cite=\"https:\/\/eclecticlight.co\/2021\/10\/03\/last-week-on-my-mac-web-woes-worsen\/\">\n<p>Since the first of those security certificates expired on 29 September, there&rsquo;s been a steady stream of comments from ordinary users, those operating small websites, developers, and system administrators, documenting far more extensive consequences than any of us had anticipated.<\/p>\n<p>[&#8230;]<\/p>\n<p>When your browser blocks or warns you about a site you want to visit, don&rsquo;t just blunder on assuming that you&rsquo;re right. You might be, but you have at least to wonder what&rsquo;s wrong, and whether that&rsquo;s a warning in itself. Check the site&rsquo;s certificates and think through the implications of any error messages. If the identity on the leaf certificate doesn&rsquo;t match the site you&rsquo;re trying to connect to, be extremely wary, as that&rsquo;s a common ploy of impersonators.<\/p>\n<\/blockquote>\n\n<p><a href=\"https:\/\/eclecticlight.co\/2021\/10\/04\/how-safari-15-checks-a-secure-connection\/\">Howard Oakley<\/a>:<\/p>\n<blockquote cite=\"https:\/\/eclecticlight.co\/2021\/10\/04\/how-safari-15-checks-a-secure-connection\/\">\n<p>To understand why current versions of Safari appear to be having problems connecting to some sites, particularly those affected by the recent Let&rsquo;s Encrypt certificate changes, I&rsquo;ve been exploring what&rsquo;s recorded in the Unified log. This article casts more light on the checks which Safari runs, and how they can fail.<\/p>\n<\/blockquote>\n\n<p>See also: <a href=\"https:\/\/old.reddit.com\/r\/applehelp\/comments\/pyoxme\/osx_1010_identrust_dst_root_ca_x3_expiry_fix\/\">Reddit<\/a>.<\/p>\n\n<p>Previously:<\/p>\n<ul>\n<li><a href=\"https:\/\/mjtsai.com\/blog\/2021\/09\/29\/safari-15-for-mac\/\">Safari 15 for Mac<\/a><\/li>\n<\/ul>\n\n<p id=\"some-web-sites-will-stop-working-with-el-capitan-and-older-update-2021-10-08\">Update (2021-10-08): See also: <a href=\"https:\/\/old.reddit.com\/r\/sysadmin\/comments\/py3wsw\/lets_encrypt_dst_root_ca_x3_expiry_certificate\/\">Reddit<\/a>, <a href=\"https:\/\/community.letsencrypt.org\/t\/os-x-10-11-clients-not-connecting-to-site-with-lets-encrypt-certificates\/161576\/11\">Let&rsquo;s Encrypt<\/a>.<\/p>\n\n<p id=\"some-web-sites-will-stop-working-with-el-capitan-and-older-update-2021-11-12\">Update (2021-11-12): <a href=\"https:\/\/eclecticlight.co\/2021\/10\/30\/how-to-deal-with-a-site-with-a-broken-certificate\/\">Howard Oakley<\/a>:<\/p>\n<blockquote cite=\"https:\/\/eclecticlight.co\/2021\/10\/30\/how-to-deal-with-a-site-with-a-broken-certificate\/\">\n<p>Many users are continuing to report problems trying to connect to some websites, which reportedly have broken certificates. This comes a month after the fiasco with the Let&rsquo;s Encrypt root certificate, and affects some other root certificate authorities, including IdenTrust. This article explains how you can deal with these and similar problems in both current and older versions of macOS.<\/p>\n<\/blockquote>","protected":false},"excerpt":{"rendered":"<p>Scott Helme (Hacker News): On 30th September 2021, the root certificate that Let&rsquo;s Encrypt are currently using, the IdentTrust DST Root CA X3 certificate, will expire. You may or may not need to do anything about this Root CA expiring, but I&rsquo;m betting a few things will probably break on that day so here&rsquo;s what [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"apple_news_api_created_at":"2021-09-24T20:49:59Z","apple_news_api_id":"1d7522df-02e6-4665-9778-4a1ae4bd0015","apple_news_api_modified_at":"2022-02-17T14:26:37Z","apple_news_api_revision":"AAAAAAAAAAAAAAAAAAAABw==","apple_news_api_share_url":"https:\/\/apple.news\/AHXUi3wLmRmWXeEoa5L0AFQ","apple_news_coverimage":0,"apple_news_coverimage_caption":"","apple_news_is_hidden":false,"apple_news_is_paid":false,"apple_news_is_preview":false,"apple_news_is_sponsored":false,"apple_news_maturity_rating":"","apple_news_metadata":"\"\"","apple_news_pullquote":"","apple_news_pullquote_position":"","apple_news_slug":"","apple_news_sections":"\"\"","apple_news_suppress_video_url":false,"apple_news_use_image_component":false,"footnotes":""},"categories":[2],"tags":[248,31,1137,2120,30,39,1199,1381,1891,2077,179,103,48,581,1659,1227,96,388],"class_list":["post-33724","post","type-post","status-publish","format-standard","hentry","category-technology","tag-android","tag-ios","tag-ios-9","tag-lets-encrypt","tag-mac","tag-macappstore","tag-mac-os-x-10-11","tag-macos-10-12","tag-macos-11-0","tag-macos-12","tag-openssl","tag-safari","tag-security","tag-ssltls","tag-this-blog","tag-top-posts","tag-web","tag-wikipedia"],"apple_news_notices":[],"_links":{"self":[{"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/posts\/33724","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/comments?post=33724"}],"version-history":[{"count":7,"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/posts\/33724\/revisions"}],"predecessor-version":[{"id":35050,"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/posts\/33724\/revisions\/35050"}],"wp:attachment":[{"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/media?parent=33724"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/categories?post=33724"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/mjtsai.com\/blog\/wp-json\/wp\/v2\/tags?post=33724"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}