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- The Guardian - Technology
- UK watchdogs urged to tackle suicide social media content after death of girl, 14
UK watchdogs urged to tackle suicide social media content after death of girl, 14
Adriana Retyte took her own life after viewing ‘high-risk’ material on the video-sharing platform TikTok
A 14-year-old schoolgirl’s death after TikTok served her suicide content has prompted renewed calls for UK watchdogs to crack down on “toxic” social media feeds.
Adriana Retyte, a pupil at Langley school in Norfolk, took her own life after she viewed videos and images related to suicide on the video-sharing platform, according to a coroner who last week found her access to the material on TikTok “may have played a significant part in her decision to take her life”.
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© Photograph: The Good Brigade/Getty Images

© Photograph: The Good Brigade/Getty Images

© Photograph: The Good Brigade/Getty Images
- EnviroLink Network
- California Wildfires Damage Homes, Exmoor Dark Skies Festival Marks a Decade — Today’s Environmental Briefing for Sat, Oct 17 2026
California Wildfires Damage Homes, Exmoor Dark Skies Festival Marks a Decade — Today’s Environmental Briefing for Sat, Oct 17 2026
Environmental change is being measured in forests cleared, crops stressed and species pushed from their habitats. But the response is also being shaped by decisions about money, land and technology, and by people trying to protect both livelihoods and the places they depend on.
Brazil’s latest figures offer one of the clearest signs of progress: forest clearing in the Amazon fell to 3,335 square kilometers in the year ending July 31, 2026, 42% below the previous year and the lowest level since records began in 1988. The Cerrado also saw a decline. The drop comes ahead of a presidential run-off in which the rainforest’s future is a key issue. Whether the reduction lasts remains uncertain.
Elsewhere, the costs of adapting to environmental pressures are immediate. Drought has left England’s pumpkins smaller than usual, with growers warning the crop could be the worst on record. In Southern California, wildfires have damaged or destroyed six homes, while a firefighter suffered heat exhaustion. And in the UK, proposals to cut hundreds of millions of pounds from the heat pump grant scheme could affect support for households switching from gas, oil or LPG boilers.
These stories sit alongside questions about what governments choose to prioritize. US voters in battleground states want candidates to discuss climate change, but candidates have largely stayed quiet. In Britain, Chancellor John Healey has made a growth case for Heathrow’s proposed third runway, while the prime minister has not backed the project. The government is studying consultation responses. The choices are practical as well as political: how to cut emissions, where to direct public funds and whose concerns shape decisions.
On the ground, communities are building their own responses. In Sergipe, women shellfish gatherers are resisting mangrove degradation and fighting for access to the areas where they work. In coastal Indonesia, Wisye Sahambangung leads a women’s group restoring mangroves and creating economic opportunities. Their work connects habitat protection with income and access to natural resources.
Other reports show how easily conservation efforts can create new pressures. Researchers found fewer wild pollinators in areas with higher concentrations of honeybees, which were observed bumping into or chasing other pollinators from flowers. The finding complicates the idea that more beekeeping automatically helps pollinators. In western states, efforts to reduce wolf numbers raise questions about the animals’ social lives and their role in nature. Meanwhile, countries are falling short of pledged funding and ocean-protection goals ahead of the UN biodiversity conference, COP17.
Technology and spectacle bring their own questions. Starlink’s reported restrictions in Ukraine have prompted US senators to seek an investigation into who imposed them, while the service remains important to Ukraine’s wartime operations. At a different scale, Belfast Harbour is to test zero-emission transport and energy systems with £15m in funding.
The Exmoor Dark Skies Festival, with about 80 events planned, offers another way people encounter the natural world: through walks, astronomy sessions and moonlit swims. The weeks ahead will show whether policy commitments match the scale of environmental pressures, and whether local efforts can endure with the resources and access they need.
The post California Wildfires Damage Homes, Exmoor Dark Skies Festival Marks a Decade — Today’s Environmental Briefing for Sat, Oct 17 2026 first appeared on EnviroLink Network.
- The Guardian - Technology
- The power of AI is worrying senior Labour figures – as is the fear of ‘falling behind the public’
The power of AI is worrying senior Labour figures – as is the fear of ‘falling behind the public’
Westminster appears to be waking up to warnings over AI safety, with concerns over its use by extremist groups and bad actors
“I have this sense that, within a few months, AI is going to be all anyone is talking about,” said one cabinet minister, with an ominous stare.
It was Labour conference, with everyone from ministers to activists jubilant at Andy Burnham’s takeover and a bounce in the polls after the change of leader.
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© Photograph: MASTER/Getty Images

© Photograph: MASTER/Getty Images

© Photograph: MASTER/Getty Images
October Patch Tuesday: 1,408 CVEs, 1 exploited flaw and a SharePoint surprise
Microsoft’s October 2026 Patch Tuesday is the year’s largest release, with 1,408 CVEs requiring customer action, 72 of them rated critical. September, the previous high, carried 963. One CVE is already exploited: CVE-2026-96951, a Windows Shell flaw that bypasses Mark of the Web. Two were publicly disclosed before release, in the .NET Framework and the MessagePack-CSharp library. Separately, on 25 September Microsoft reported attacks against CVE-2026-65660, a SharePoint Server flaw fixed in August. Readiness recommends a Patch Now scheduling for Windows, Office, Exchange and the developer tooling, and a standard release schedule for SQL Server. The Readiness team has published an infographic summarising deployment risk by product family.
Known issues
On 14 October, Microsoft added a known issue to this month’s Windows 11 updates, KB5127648 for versions 24H2, 25H2 and 26H2, and KB5127646 for 26H1. Non-admin users might be unable to open Remote Desktop connections to devices that have Administrator protection enabled, with error 0xC000000D. The issue started with September’s non-security preview update. The Windows 11 security baselines enable Administrator protection by default, so test remote access to managed hosts before broad deployment. Microsoft’s mitigation is to turn off Administrator protection temporarily through your policy management tool, and a fix will follow in a future update.
Two issues remain open:
- Some USB Audio Class 1.0 devices might fail to start or produce no sound. The 14 September out-of-band update resolved part of this, and for the remaining symptoms Microsoft directs IT administrators to Microsoft Support for Business.
- Windows Server Update Services still does not display synchronisation error details on Server 2025 and Server 2022. Microsoft removed the function to address CVE-2025-59287 and offers no workaround.
And three are now closed:
- The incorrect “Microsoft Defender Antivirus is turned off” notifications, still open when we published in September, were fixed by Defender Antivirus update 4.18.26080.4, released on 17 September.
- On Windows 11, the October update fixes Explorer failing to start after sign-in on multi-user systems such as Azure Virtual Desktop with FSLogix, which left users at a black screen.
- On Windows 10, Windows 11 23H2 and Server 2016 and 2019, it fixes File History failing to back up or restore and showing a false “Reconnect your drive” message.
Major revisions and mitigations
Between the September and October releases, from 9 September to 12 October, Microsoft’s Security Update Guide notifications covered 111 entries for Microsoft’s own products, not counting Chromium republications for Edge. Of those 111, 90 are true revisions rather than new entries. September’s window had one.
- On 17 September, 84 of September’s CVEs gained Office for Mac updates. Each revision note tells customers running affected Mac software to “install the update for their product to be protected”.
- On 16 September, Microsoft corrected the scoring of three critical SQL Server remote code execution flaws from September, CVE-2026-67378, CVE-2026-67631 and CVE-2026-67643. The scores now record that “an attacker does not require any privileges”. Microsoft calls this an informational change.
- On 25 September, Microsoft revised CVE-2026-65660, a SharePoint Server remote code execution flaw fixed in August, to state that it “had reliable evidence of observed attacks against exploitation of this vulnerability”. CISA added it to its list of known exploited vulnerabilities the same day. The Security Update Guide still shows “Exploited: No” for this CVE, so a report filtered on that flag will miss it. If any SharePoint server lacks the August update, install it now.
- Of the 21 new entries, 18 are critical cloud-side flaws in Azure, Microsoft 365 Copilot, Dataverse and Fabric, all marked “Customer action required: No”. Two are Edge flaws, and one is CVE-2026-96940 in Exchange Server, published on 2 October and covered below.
Microsoft has published no mitigations and no workarounds in the October release.
Windows lifecycle and enforcement updates
These support milestones passed with this release on 13 October, as scheduled:
- Office 2021 retail and Office LTSC 2021, including Skype for Business LTSC 2021, reached the end of support.
- Windows 10 Enterprise 2016 LTSB and Windows 10 IoT Enterprise LTSB 2016 reached the end of extended support.
- Extended Security Updates for Windows Server 2012 and 2012 R2 ended. Year three was the last, so the October update is the final one for both.
- Windows 11 Home and Pro version 24H2 reached the end of updates.
- Windows Server 2022 moved to extended support, which runs to 14 October 2031.
The next milestones fall on 10 November 2026, the date of November’s Patch Tuesday. .NET 8 and .NET 9 reach the end of support, as do PowerShell 7.4 and 7.5. Windows 11 Enterprise and Education 23H2, and IoT Enterprise 23H2, reach the end of updates, and Microsoft says November’s update “will be the last update available for these editions”.
Microsoft also starts or tightens several enforcement changes with this release:
- Windows 11 24H2, 25H2 and 26H2, and Windows Server 2025, now restrict NTLMv1-derived credentials for single sign-on by default. Where Credential Guard is off, Microsoft warns this “might affect Wi-Fi, Ethernet and VPN connections that use MS-CHAPv2-based authentication” (KB5066470).
- AD FS Distributed Key Manager container permissions move into enforcement mode. Supported servers remediate automatically, but Server 2012 and 2012 R2 need manual remediation (KB5121391).
- ReFS volumes on removable media enter an audit phase, and blocking is enabled by default from the January 2027 update (KB5130741).
- The Windows Production PCA 2011 Secure Boot certificate, used to sign the Windows boot loader, expires on 19 October. Devices without its replacement, Windows UEFI CA 2023, keep starting and updating normally, but they stop receiving new early-boot protections (KB5062710).
Microsoft’s test guidance for this release runs to 496 Windows entries, 41 of them flagged as high risk, against 466 and 55 in September. Printing, scanning and font rendering account for 31 of the 41. The Readiness team recommends these testing priorities:
- Printing. Print documents with mixed fonts from 32-bit and 64-bit applications to physical and virtual printers. Add network printers by discovery and by IP address, and print through a shared print server, a USB printer and a PostScript driver.
- Downloaded files. The exploited Shell flaw bypasses Mark of the Web, so open files and shortcuts downloaded from the internet and confirm the SmartScreen and security warnings still appear.
- Remote access. Test Remote Desktop with a non-admin account against hosts that have Administrator protection enabled, and test Wi-Fi and VPN connections that use MS-CHAPv2.
- Application installs. Install, repair and uninstall a representative set of MSI packages, including packages with script custom actions. Windows Installer takes 38 fixes this month.
- Network servers. Run DNS servers (52 fixes) and DHCP servers (18) under load, and confirm leases, zone transfers and conditional forwarders behave as before.
Each month, we break down the update cycle into product families, as defined by Microsoft, with the following groupings.
Browsers
For the third month in a row, Microsoft’s Patch Tuesday release lists no browser CVEs. Edge security fixes arrived between releases instead. Between 9 September and 12 October, Microsoft published 414 CVEs for Microsoft Edge in the Security Update Guide: 409 republished from Chromium and five specific to Edge. None carries an exploited flag, and no Edge release in that period reported an exploit in the wild.
Microsoft Windows
Windows takes 1,122 CVEs this month, 42 of them critical. Elevation of privilege accounts for 617 entries, information disclosure for 200 and remote code execution for 179. Of the 42 critical entries, 31 are remote code execution, nine are elevation of privilege and two are spoofing.
- The exploited flaw is CVE-2026-96951, a Windows Shell security feature bypass that evades Mark of the Web defences. An attacker must convince a user to open a crafted file or follow a link. CISA added it to its list of known exploited vulnerabilities on 13 October, with a remediation date of 16 October.
- DHCP takes 18 fixes, six of them critical remote code execution: five in DHCP Server and one in the DHCP client. DNS Server takes 52, 10 of them remote code execution, though none is critical. Critical remote code execution also affects Hyper-V, Message Queuing, Microsoft QUIC, the Remote Desktop Gateway, Windows Deployment Services, Active Directory Domain Services, NDES and the multicast transport driver.
- In file and image handling, the Raw Image Extension has three critical fixes, one of them a CVE assigned by Cisco Talos, and the PostScript printer driver takes three more. Text shaping takes two, and Media Foundation, the codecs library, the video decoder, GDI+, the graphics component and the Windows PDF component take one each.
- The virtualisation-based security enclave takes eight fixes, five of them critical elevation of privilege.
- The most-patched areas are DNS Server at 52, Win32k at 48, the Windows Kernel at 46 and Windows Installer at 38.
Add this Windows update to your Patch Now schedule. Every client needs the fix for the exploited Shell flaw, and DHCP servers and Hyper-V hosts need the critical server-side fixes.
Microsoft Office
Microsoft released 180 Office CVEs this month, 26 of them critical, and remote code execution accounts for 107.
- Client updates on Windows are Click-to-Run only, for Microsoft 365 Apps, Office LTSC 2021 and Office LTSC 2024. Office for Mac updates ship in the same release this month, rather than nine days later as they did in September. Excel takes 69 fixes, 11 of them critical. Word takes 22, Access 13, Outlook 10 with five critical, PowerPoint nine with four critical, and Visio three, all critical.
- SharePoint Server Subscription Edition takes 34 CVEs in KB5002927, two of them critical. SharePoint Server 2016 and 2019 left extended support on 14 July 2026, and two of this month’s flaws list them as affected with no update: CVE-2026-69943 for both versions and CVE-2026-97783 for 2019.
- Office Online Server takes 43 CVEs in KB5002928. Skype for Business Server takes three, in KB5132779 for 2015 CU13, KB5131693 for 2019 CU8 and KB5131692 for Subscription Edition CU1.
Add these updates to your Patch Now schedule, because 25 of the 26 critical entries affect Excel, Outlook, PowerPoint, Visio and Word.
Microsoft Exchange and SQL Server
Exchange has one critical entry this month and SQL Server has none.
- Exchange Server has seven CVEs across 2016 CU23, 2019 CU14 and CU15, and Subscription Edition: one critical remote code execution, CVE-2026-70571, five elevations of privilege and one spoofing flaw. Six are fixed by the 13 October updates: KB5128895 for Subscription Edition, KB5128896 for 2019 CU15, KB5128897 for 2019 CU14 and KB5128898 for 2016 CU23.
- The seventh, CVE-2026-96940, was published on 2 October. Microsoft lists it against a separate set of updates released that day, KB5129955 to KB5129958, not against the 13 October updates, so confirm both sets are installed. Microsoft rates both CVE-2026-96940 and the critical entry as “Exploitation More Likely”..
- SQL Server has 22 CVEs, none of them critical: eight remote code execution, seven elevation of privilege, four information disclosure and three denials of service. Each supported branch gets a cumulative update and a GDR: 2025 (KB5126967, KB5128492), 2022 (KB5126934, KB5128493), 2019 (KB5128494, KB5128495) and 2017 (KB5128496, KB5128497).
Exchange goes on the Patch Now list. SQL Server goes on the Schedule list because none of its 22 entries is critical. If September’s SQL Server update is still outstanding, install it first.
Microsoft Developer Tools
Microsoft released 66 CVEs across its developer tooling this month: two critical, 63 important and one moderate. Remote code execution accounts for 18 entries and elevation of privilege for 13.
- Both critical entries also affect Windows. CVE-2026-105016 is a remote code execution flaw in Microsoft QUIC that needs no authentication or user interaction, and it affects .NET 8, 9, 10 and 11 on Windows and Visual Studio 2022 and 2026. CVE-2026-96222 is an AD FS certificate validation flaw that Microsoft lists against both the .NET Framework and Windows Server.
- Two entries were publicly disclosed before release. CVE-2026-108398 in the .NET Framework lets an authenticated attacker bypass Windows Defender Application Control. CVE-2026-92707, a denial-of-service vulnerability in the MessagePack-CSharp library assigned by GitHub, affects Visual Studio and the ASP.NET Core SignalR MessagePack protocol.
- Visual Studio Code has 10 fixes, five of them security feature bypasses, and PowerShell 7.4, 7.5 and 7.6 take two.
Add these updates to your Patch Now schedule, starting with the .NET updates that carry the QUIC fix.
Adobe (and third-party updates)
Adobe published 11 security bulletins on 13 October, covering 175 CVEs across ColdFusion, Experience Manager, Commerce, Photoshop, Bridge, FrameMaker, Dimension, the Substance 3D tools and the Content Credentials SDK. None is rated priority 1, and Adobe is not aware of exploits for any of them. No Acrobat or Reader security update for this month. I mentioned last month that we are in for a few months of extraordinary patch releases. Harking back to 2003 (when I started work on the nascent field of Microsoft patch management), with Microsoft releasing just 51 updates, anything over a 1000, much less 1400 CVE entries would have been unimaginable. I don’t think that we are at a “patch maximum” yet — but I hope that things calm down soon.

Xbow spent $40K on AI and cracked Google Chrome wide open
A chain of vulnerabilities in Google’s Chrome browser could have enabled researchers to take control of one billion Windows machines worldwide — and it cost them just $40,000 in AI compute time to discover it.
Researchers at Xbow USA worked for six days on developing the exploit, which earned them a $250,000 bug bounty from Google, the first under the new 2026 rules.
They chose OpenAI’s GPT-5.6 Sol for the task to demonstrate what’s possible with a publicly available model rather than a specialist security implementation. They used it to search Chrome’s source code, test ideas, and build proofs of concept, while they set the strategy, chose where to look, and checked its work.
They successfully chained together a vulnerability to escape first from the sandbox containing the V8 JavaScript engine and then from Chrome’s operating-system process sandbox, launching a Windows app from within a malicious web page.
Xbow presented its findings to Google, which fixed the flaws. The researchers set out all the details as to how the exploit was developed in a blog.

Locked Down Passkey and Keychain Backups
I remain unhappy with Apple’s passkey backup story. There’s little documentation about this, but from what I can tell:
There are no automatic versioned backups. (Syncing is not backup because it doesn’t protect you against human error, bugs, or attacks.)
Even if you have a Time Machine backup, it’s not possible to restore it to the same Mac without logging into iCloud. This could be a problem if your account is locked or compromised.
Restoring it to a different Mac is impossible because the decryption key is stored in the other Mac’s Secure Enclave. Apple is protecting you from accessing your own backup, even though the keychain is already an encrypted file, protected by the password that you set. (And the Time Machine or clone drive that it’s stored on is probably encrypted, too.)
The Passwords app can now export passkeys, but you cannot create an export file that you can import back into Passwords on another Mac. You can only export to a third-party password manager that’s installed on the same Mac (which may require a working Apple account). Even then, this does not include passkeys for Apple services; they don’t show up in the Passwords app. There are also some other restrictions around shared items and Sign In with Apple.
The above is last year’s news, but I don’t think I had written it all in one place before. The new bad news is that, as of macOS 26.4, these problems now affect regular passwords, not just passkeys. (You do have more flexibility to export passwords, though.)
Historically, you could copy the login keychain file from one Mac to another and be able to open it on the destination Mac by providing the password to that keychain. As of macOS Tahoe, this does not appear to work for Macs which use Secure Enclave.
[…]
From that, it appears that unlocking the login keychain requires more than the password because the keys it unlocks are tied to the Secure Enclave of the Mac where the keychain was created. With the decryption keys stored in the source Mac’s Secure Enclave, manually copying the keychain to another Mac and then unlocking it won’t work. The password you have for the keychain may be correct, but the actual keys needed to decrypt its contents won’t be available on the destination Mac.
According to Apple, all Apple silicon Macs, as well as some Intel Mac models, have the secure enclave processor, so the issue affects millions of Mac users.
[…]
If anything happens to your Mac, if it’s stolen or becomes inoperable, your login keychain is also lost, unrecoverable, even if you have a copy of the login keychain file! This is a stunning development that has left me bewildered and irate. WTF was Apple thinking? To my knowledge, Apple did not even publicize the change in Tahoe.
[…]
How does Migration Assistant handle the situation on Tahoe? I don’t know. I would guess that since Migration Assistant still has access to the old Mac, it simply decrypts the old login keychain and copies the login keychain entries to the new login keychain on the new Mac, rather than transferring the keychain files directly.
[…]
I recommend that you open your login keychain with the Keychain Access app (now located in
/System/Library/CoreServices/Applications) and check what’s in there, the data that you’re in danger of losing. Whether you realize or it not, many apps use the login keychain. For example, Google Chrome and other Chromium browsers store passwords in the login keychain. MailMate stores email account passwords in the login keychain. The open source RSS reader Vienna stores website passwords in the login keychain. The Zoom app also uses the login keychain. My Developer ID code signing certificate is stored in the login keychain; if I’m not mistaken, I believe that Apple’s own Xcode put it there. And of course, any items that you’ve manually added to the login keychain would be lost if the keychain file could not be unlocked.
I have confirmed that a login.keychain-db copied from my Mac mini M4 Pro to a virtual machine (VM) running macOS Tahoe 26.6.2 cannot reveal any of its secrets to the Keychain Access app on the VM, as it refuses to accept the valid password. Not only that, but Keychain Access running in a VM cannot access the login.keychain-db keychain copied from another Tahoe VM, although neither has been anywhere near a Secure Enclave.
If you intend migrating manually between Macs, don’t waste time trying to copy across the login keychain, as it’s not likely to work, and its secrets will remain.
[…]
I performed test migrations between VMs, and demonstrated that Migration Assistant does copy the contents of the login keychain successfully to the destination Mac.
I think this only happens if you migrate over a network, with the old Mac acting as a server. I prefer to connect the old Mac using Target Disk Mode, but in that case Migration Assistant wouldn’t be running on the old Mac so the special sauce wouldn’t work. Likewise if I were trying to do the migration using a third-party cloning app.
- Loss of physical access to a Mac running 26.4 or later prevents access to any items stored in its login keychain.
- Hardware failure requiring logic board replacement may have the same effect on restoring the contents of its login keychain (assuming that migration from a backup doesn’t work).
- Restoring an Apple silicon Mac in DFU mode may be similar in effect.
What I don’t know yet is whether you can unlock and access any login keychain written by macOS 26.4 or later and migrated from a backup accessed directly from a different Mac. This would occur in one-Mac migration, when Migration Assistant uses a backup of a Mac not acting as a Migration server. This would only be possible if the backup also stored the additional secret required to access the login keychain, which seems unlikely.
[…]
Apple’s documentation for macOS Tahoe and the copying of keychains makes no mention of this change, in spite of its serious consequences and the change being made almost six months ago.
It there states “If you didn’t use Setup Assistant, the best way to copy your keychains to a new computer is to export and then import them using Keychain Access”. However, Keychain Access can only export some keychain items including certificates and keys, but not passwords. And to do that, the Mac must be able to unlock and access those items in the source keychain. Thus, Apple’s recommendations are out of date and will now fail.
rsUSA0 (via Jeff Johnson):
When upgrading to macos 27 Golden Gate, I erased my system through recovery to do a clean install. I planned to manually migrate data back to the computer from an external drive clone of Macintosh HD and a Time Machine backup. This has worked well in the past and eliminated system bloat.
When I manually migrated my login keychain, it opened, showed entries, but it wouldn’t accept my password to reveal any actual passwords. The window shakes like I’m using the wrong password. I’m 100% sure I’m using the correct password. I also tried every password I’ve ever used and I’m certain it’s not a password issue.
Perhaps even restoring to the same Mac failed because the clean install wiped the key stored in the Secure Enclave. [Update (2026-10-01): See update below.]
Some people who read my previous blog post misunderstood the issue, because they didn’t know that the macOS login keychain is distinct from iCloud Keychain.
[…]
In the Keychain Access app, you can see two separate default keychains, one of which is the login keychain. The other default keychain is named “iCloud” if you’ve enabled iCloud Keychain, “Local Items” if not. There’s actually a longstanding issue with this keychain analogous to the newer issue with the login keychain.
[…]
Mac users like myself who forsake iCloud Keychain face the prospect of no disaster recovery for the Local Items keychain. My habit is to manually create a new password item in the login keychain and only then supply the credentials to an app, for example, Safari AutoFill. Ironically, the login keychain change brought by macOS 26.4 sabotages my password backup procedure[…]
Today, I got my new Mac mini M6. When I started setting up the new machine, it asked me to update to macOS 27, so I followed the instructions.
[…]
After signing in to iCloud, it asked me to enter the passcode of one of my Apple devices. I entered the correct passcode and even tried the passcodes for all of my devices, but I keep getting the same message:
Verification Failed
There was an error verifying the passcode of your iPhone
I don’t like having to rely on iCloud.
Previously:
- SuperDuper’s “Follow-Up”
- macOS 26.4
- 2025 Six Colors Apple Report Card
- Locked Out of Apple Account Due to Gift Card
- Downloading Xcode With a Passkey
- iOS and iCloud Keychain Are Hostile to Backups
- Passkeys Credential Exchange
- Passkeys: A Loss of User Control?
- Fixing iCloud Keychains, and Backing Them Up
Update (2026-10-01): TN3137 has been updated for macOS 26.4:
Historically each file-based keychain was a standalone file. You could, for example, copy a keychain file from one Mac to another and still use it, as long as you knew the keychain password.
In macOS 26.4 and later that’s no longer the case. A keychain file might reference a protected entropy file. To unlock such a keychain you need both the keychain password and the protected entropy file.
[…]
These protected entropy files are stored in /var/db/SystemKeys. If you’re creating a backup product, make sure to back up that directory. Without it, the keychain files that you back up might be useless.
[…]
The /var/db/SystemKeys directory is not directly accessible, even when running as root, so you can’t copy a protected entropy file in the normal way. To access it, disable System Integrity Protection (SIP).
First things first: I don’t think turning off SIP every time you make a backup is a real solution. And I don’t understand what problem Apple is really trying to solve with protecting the entropy file; it seems like they don’t trust their own encryption. Lastly, it’s not explicitly stated, but I don’t think copying the entropy file helps with backing up passkeys.
That aside, I find the details both illuminating and confusing. This probably explains the rsUSA0 case above, where restoring to the same Mac didn’t work. The key wasn’t stored in the Secure Enclave but rather in the entropy file on the SSD, which had been wiped. This also suggests a simpler way for Migration Assistant to work; it could have special access to copy the entropy file without having to actually open the keychain.
It also seems to be saying that, if you turn off SIP and copy the entropy file, you can then access your keychain backup from another Mac. But I’m not sure how to square that with Apple’s keychain documentation:
Keychain items are encrypted using two different AES-256-GCM keys: a table key (metadata) and a per-row key (secret key). Keychain metadata (all attributes other than kSecValue) is encrypted with the metadata key to speed searches, and the secret value (kSecValueData) is encrypted with the secret key. The metadata key is protected by the Secure Enclave but is cached in the Application Processor to allow fast queries of the keychain. The secret key always requires a round trip through the Secure Enclave.
How can copying the entropy file work if the Secure Enclave is required? My guess is that the entropy file itself is encrypted (NSFileProtection) using the Secure Enclave. So accessing it on the original Mac does require going through the Secure Enclave. But when you make a backup, the entropy file gets decrypted. Maybe accessing the keychain on the second Mac causes file protection to be re-applied to the contents of /var/db/SystemKeys, so then it becomes protected by that Mac’s Secure Enclave.
Previously:
Update (2026-10-02): Dave Nanian (Mastodon):
This is obviously not a good user solution, because no one is going to boot to Recovery, turn off SIP, back up, boot back to Recovery, and turn SIP back on. Thinking they would do so is kind of crazy.
[…]
SuperDuper handles this situation. When you make a bootable copy, the required keys are copied without requiring any special steps.
SuperDuper itself can’t read the entropy file, but it uses Apple’s asr tool to make bootable backups, and that has special access. (Unfortunately, it can’t update the entropy file without making a fresh bootable backup, but in practice I don’t expect it to need updating.) I had not been bothering to make most of my backups bootable, since in most cases I just want to restore to an internal SSD, not actually boot from the backup. But I now think it makes sense to choose bootable backups as the default.
I won’t expand on my feelings any further than by saying that in my 37 years as an Apple developer, I have never come across anything so shameful.
Unfortunately, it seems like the keychain stuff was just the warm-up act.
Update (2026-10-05): Howard Oakley:
[macOS 26.4] Added the protected directory at /var/db/SystemKeys to backups of Data volumes, and protects them in backups.
So Time Machine does back up the entropy file. I missed this because I didn’t see /var/db in my backups, but it turns out that they do have /private/var/db/SystemKeys and are just missing the /var symlink.
Update (2026-10-07): Jeff Johnson:
The
-soption to thesecurity show-keychain-infois not yet documented inman security, not even on the latest version of macOS Golden Gate. Moreover, the-soption does not work on macOS Sequoia and earlier. In general, thesecurity show-keychain-infocommand reveals no information unless the specified keychain is unlocked, which makes it impossible to discover the salt of a keychain file that you can’t currently unlock. However, as long as you already have the entire contents of the /var/db/SystemKeys directory from the macOS volume on which a keychain file was created, the inability to determine the keychain file’s salt beforehand shouldn’t be much of a problem, because in practice there are typically only a few salt files, so you can simply copy them all to another macOS volume.[…]
You don’t actually have to disable SIP to add files to the /var/db/SystemKeys directory, because you can do so from another boot volume. You have to boot into recovery anyway in order to disable SIP, so you could simply edit /var/db/SystemKeys from recovery rather than disabling SIP on the non-recovery volume.
The
security unlock-keychaincommand lacks an option to specify the location of an entropy file or to provide the file data directly, so unfortunately a login keychain can’t be unlocked from the recovery volume, only from a volume where you can add files to the /var/db/SystemKeys directory.
Two-Tier Encryption in the UK
The Post reported that UK security officials had issued such a TCN, in secret, in January 2025, requesting that Apple create a way to access encrypted iCloud data belonging not just to UK users, but to Apple users worldwide. The chutzpah of it all was astonishing.
Apple’s position (privately, since they were prohibited from commenting publicly on the reported TCN) showed fidelity to its previous stance: deliberately weakening end-to-end encryption, for whatever purpose or for whomever the intended beneficiary, would make every user less secure. So the dispute became the UK government saying it needed access, Apple saying it couldn’t decrypt the data, and the UK effectively replying: then change the system so that you can.
[…]
Faced with a legal order that would have required it to change the security architecture on which ADP depended, Apple found a third option: stop offering the feature that made this dilemma exist in the first place. It reverted affected UK iCloud data to Standard Data Protection, where Apple does hold the keys and can respond to lawful legal process (except the baseline categories that stay end-to-end encrypted either way). This satisfied the underlying legal requirement without ever building a ‘backdoor’.
Apple said the decision to withdraw ADP in the UK left them “gravely disappointed”. There was, however, an important disclaimer. Apple only stopped allowing new UK users to turn on Advanced Data Protection.
For users in the UK who have already enabled Advanced Data Protection, Apple will soon provide additional guidance. Apple cannot disable ADP automatically for these users. Instead, UK users will be given a period of time to disable the feature themselves to keep using their iCloud account.
I wonder whether Apple will actually lock users out of their accounts if they don’t turn off ADP or whether they’ll quietly not enforce it like with Emergency SOS via satellite.
In July 2026, Apple lodged a fresh complaint at the Investigatory Powers Tribunal, which became public the following month. Then, on the 11th of September 2026, U.S. Senator Ron Wyden (a Democrat) and Republican Congressman Warren Davidson called on the UK’s Investigatory Powers Tribunal to open up its proceedings concerning Apple’s encrypted-data dispute.
[…]
On the 17th of September The Daily Telegraph reported that Apple had asked the Investigatory Powers Tribunal to remove restrictions that gag them from confirming the existence of the reported TCN.
Previously: