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Updated Apple's latest update to macOS Catalina appears to have broken SSH for some users.

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Developer Tyler Hall published a blog post on Monday detailing the issue, but removed it after his writeup got noticed.

The issue is that under Apple's macOS 10.15.4 update, released on March 24, trying to open a SSH connection to a port greater than 8192 using a server name, rather than an IP address, no longer works – for some users at least. SSH is a Swiss army knife that can be used to securely connect to remote machines to run commands, transfer files and other data, and so on.

Jun 23, 2020 The macOS Catalina 10.15.3 update improves the stability, reliability, and security of your Mac, and is recommended for all users. Optimizes gamma handling of low gray levels on Pro Display XDR for SDR workflows when using macOS; Improves multi-stream video editing performance for HEVC and H.264-encoded 4K video on the MacBook Pro (16-inch, 2019).

The Register asked Hall to elaborate on his findings but he declined, citing the possibility that the problem might be particular to his set up rather than a bug in the software Apple shipped.

Wi-Fi of more than a billion PCs, phones, gadgets can be snooped on. But you're using HTTPS, SSH, VPNs... right?

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Hall demonstrated similar post-publication remorse this last October when he criticized the code quality of macOS Catalina, comparing it to Windows Vista. That sentiment is shared among many other macOS users (eg: 'macOS 10.15 is chockablock with paper-cut bugs' – John Gruber). But the responses Hall received from friends within Apple led him to regret that post, too.

We asked Apple to comment but we've received no reply. Cupertino seldom addresses public criticism. Until June 2016, Apple even implied in its App Store Review Guidelines that it would look unfavorably on developers who complain publicly about rejected apps. Up to that point, its policy said, 'If you run to the press and trash us, it never helps.'

The US government's renewed antitrust scrutiny of companies like Amazon, Apple, Facebook, and Google in recent years has perhaps encouraged more caution in publicly declared tech platform policies.

The issue that Hall reported has been noted by others. A post two days ago on Apple's discussion forum complains, 'After that update I am no longer able to open a SSH connection to a port greater than 8192 using server name (instead of IP).' And three discussion participants claim they too have experienced the same issue.

One of these individuals, posting under the user name 'webdeck,' filed a bug port in Open Radar, a public iOS and macOS bug reporting site created by developer Tim Burks because Apple hides its Radar bug reporting system from the public.

The bug report reads, '/usr/bin/ssh in macos 10.15.4 hangs if used with the -p flag to specify an alternate port and used with a hostname. This was not present in macOS 10.15.3.'

There's reason to believe, however, that not all those using SSH to connect to ports greater than 8192 using a host name have experienced problems. In the Hacker News discussion, several participants report being unable to reproduce the reported bug. That suggests the interplay of other software, like package manager Homebrew, or specific configuration settings may be relevant.

If this is a bug in Apple's software, perhaps it will be fixed in macOS 10.15.5, the beta version of which was just seeded to developers. And if Apple was more transparent about the bugs it's aware of, we might understand what's going on. ®

Updated to add

Judging from Open Radar, it appears the problem is caused if you have a proxy configured. Disabling Auto Proxy Discovery, for instance, lets SSH work as normal, and re-enabling it breaks the software.

Editor's note: We're happy to clarify that Hall did not remove his October 7, 2019 post about macOS Catalina as first reported. It was merely unavailable at the time we checked. Hall has also restored the SSH post he removed previously.

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macOS Catalina updates improve the stability, performance, or compatibility of your Mac and are recommended for all Catalina users. To get these updates, choose System Preferences from the Apple menu , then click Software Update. Learn more about updating the software on your Mac.

For details about the security content of these updates, see Apple Security Updates.

  • macOS 10.15
For

macOS Catalina 10.15.5

macOS Catalina 10.15.5 introduces battery health management in the Energy Saver settings for notebooks, a new option to disable automatic prominence in Group FaceTime calls, and controls to fine-tune the built-in calibration of your Pro Display XDR. The update also improves the stability, reliability, and security of your Mac.

Battery Health Management

  • Battery health management to help maximize battery lifespan for Mac notebooks
  • Energy Saver preference pane now displays battery condition and recommends if the battery needs to be serviced
  • Option to disable battery health management
    For more information, please visit https://support.apple.com/kb/HT211094

FaceTime Prominence Preference

  • New option to control automatic prominence on Group FaceTime calls, so video tiles do not change size when a participant speaks

Calibration Fine-Tuning for Pro Display XDR

  • Controls to fine-tune the built-in calibration of your Pro Display XDR by adjusting the white point and luminance for a precise match to
    your own display-calibration target

This update also includes bug fixes and other improvements:

  • Fixes an issue that may prevent Reminders from sending notifications for recurring reminders
  • Addresses an issue that may prevent password entry on the login screen
  • Fixes an issue where System Preferences would continue to show a notification badge even after installing an update
  • Resolves an issue where the built-in camera may not be detected when trying to use it after using a video conferencing app
  • Addresses an issue for Mac computers with the Apple T2 Security Chip where internal speakers may not appear as a sound output device in Sound preferences
  • Fixes a stability issue with uploading and downloading media files from iCloud Photo Library while your Mac is asleep
  • Resolves a stability issue when transferring large amounts of data to RAID volumes
  • Fixes an issue where the Reduced Motion Accessibility preference did not reduce the speed of animations in a Group FaceTime call

Enterprise content:

  • Improves performance on certain Mac models when enabling hardware acceleration in GPU-intensive apps such as those used for video conferencing
  • Addresses an issue where Microsoft Exchange accounts were unable to sign in during account setup when using Conditional Access
  • Apple Push Notification Service traffic now uses a web proxy when specified in a PAC file via the Proxies payload
  • Resolves an issue that prevented some displays connected to MacBook Pro (16-inch, 2019) from waking from sleep when the Mac wakes
  • Major new releases of macOS are no longer hidden when using the softwareupdate(8) command with the --ignore flag
    This change also affects macOS Mojave and macOS High Sierra after installing Security Update 2020-003.

macOS Catalina 10.15.4

macOS Catalina 10.15.4 introduces iCloud Drive folder sharing, Screen Time communication limits, Apple Music time-synced lyrics view, and more. The update also improves the stability, reliability, and security of your Mac.

Finder

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  • iCloud Drive folder sharing from Finder
  • Controls to limit access only to people you explicitly invite, or to grant access to anyone with the folder link
  • Permissions to choose who can make changes and upload files, and who can only view and download files

Screen Time

  • Communication limits for controlling who your children can communicate with and be contacted by throughout the day and during downtime
  • Playback control of music videos for your children

Music

  • Time-synced lyrics view for Apple Music, including the ability to jump to your favorite part of a song by clicking a line in lyrics view

Safari

  • Option to import Chrome passwords into your iCloud Keychain for easy AutoFill of your passwords in Safari and across all your devices
  • Controls for duplicating a tab and for closing all tabs to the right of the current tab
  • HDR playback support on compatible computers for Netflix content

App Store with Apple Arcade

  • Universal Purchase support enables the use of a singular purchase of a participating app across iPhone, iPod touch, iPad, Mac, and Apple TV

Pro Display XDR

  • Customized reference modes that you can tailor to specific workflow needs by selecting from several color gamut, white point, luminance, and transfer function options

Accessibility

  • Head pointer preference for moving a cursor on the screen based on the precise movements of your head

This update also includes bug fixes and other improvements:

  • High Dynamic Range output to HDR10-compatible third-party displays and TVs connected with DisplayPort or HDMI
  • OAuth authentication support with Outlook.com accounts for improved security
  • CalDav migration support when upgrading to iCloud reminders on a secondary device
  • Addresses an issue where text copied between apps may appear invisible when Dark Mode is active
  • Resolves an issue in Safari where a CAPTCHA tile may display incorrectly
  • Fixes an issue where you may receive notifications for updated or completed reminders
  • Fixes an issue with screen brightness for the LG UltraFine 5K display after waking from sleep

Enterprise content:

  • Apple Push Notification Service traffic now uses a web proxy when specified in a PAC file
  • Resolves an issue where updating the login keychain password after resetting a user password would cause a new keychain to be created
  • After enabling ”Search directory services for certificates” in Keychain Access preferences, searching by email address in Keychain Access or Mail now locates a user certificate stored in directory services
  • When setting the DisableFDEAutoLogin key in com.apple.loginwindow, you can now sync your FileVault password with the Active Directory user password after updating the user password
  • Reinstates the ability to update or restore iOS, iPadOS, or tvOS devices by dragging .ipsw files to the device in an Apple Configurator 2 window
  • Addresses an issue where sending the EraseDevice MDM command might not cause the device to be erased
  • When logging in as an Active Directory user after using deferred FileVault enablement, the user is now prompted for their password to enable FileVault

Some features may not be available for all regions, or on all Apple devices.

macOS Catalina 10.15.3

The macOS Catalina 10.15.3 update improves the stability, reliability, and security of your Mac, and is recommended for all users.

  • Optimizes gamma handling of low gray levels on Pro Display XDR for SDR workflows when using macOS
  • Improves multi-stream video editing performance for HEVC and H.264-encoded 4K video on the MacBook Pro (16-inch, 2019)

macOS Catalina 10.15.2

The macOS Catalina 10.15.2 update improves the stability, reliability and performance of your Mac and is recommended for all users.

This update adds the following features:

Apple News

  • New layout for Apple News+ stories from The Wall Street Journal and other leading newspapers

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Stocks

  • Get links to related stories or more stories from the same publication at the end of an article
  • “Breaking” and “Developing” labels for Top Stories
  • Stories from Apple News are now available in Canada in English and French

This update includes the following bug fixes:

Music

  • Restores the column browser view for managing the music library
  • Resolves an issue that may prevent album artwork from appearing
  • Fixes an issue that may reset music equalizer settings during playback

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  • Adds support for using an iPhone or iPad to remotely control the Music and TV apps on a Mac

Photos

  • Resolves an issue that may cause some AVI and MP4 files to appear as unsupported
  • Fixes an issue that prevents newly created folders from appearing in Albums view
  • Addresses an issue where manually sorted images in an album may be printed or exported out of order
  • Fixes an issue that prevents the zoom-to-crop tool from working in a print preview

Mail

  • Addresses an issue that may cause Mail preferences to open with a blank window
  • Resolves an issue that may prevent using undo from retrieving deleted mail

Other

  • Improves the reliability of syncing books and audiobooks to your iPad or iPhone through the Finder
  • Fixes an issue where reminders may be out of order in the Today smart list in the Reminders app
  • Resolves an issue that may cause slow typing performance in the Notes app

Enterprise content

  • Fixes an issue where the user password might not be accepted at the login window after upgrading a Mac with an Apple T2 Security Chip to macOS Catalina
  • Improves compatibility with video conferencing apps on MacBook Pro models introduced in 2018
  • Users logged in as a standard user can now install apps from the App Store

macOS Catalina 10.15.1

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The macOS Catalina 10.15.1 update includes updated and additional emoji, support for AirPods Pro, HomeKit Secure Video, HomeKit-enabled routers, and new Siri privacy settings, as well as bug fixes and improvements.

Emoji

  • Over 70 new or updated emoji, including animals, food, activities, new accessibility emoji, gender-neutral emoji, and skin tones selection for couple emoji

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AirPods support

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  • AirPods Pro support

Home app

  • HomeKit Secure Video enables you to privately capture, store, and view encrypted video from your security cameras and features people, animal, and vehicle detection
  • HomeKit enabled routers let you control how your HomeKit accessories communicate over the internet or in your home
  • Adds support for AirPlay 2-enabled speakers in scenes and automations

Siri

  • Privacy settings to control whether or not to help improve Siri and Dictation by allowing Apple to store audio of your Siri and Dictation interactions
  • Option to delete your Siri and Dictation history from Siri Settings

This update also includes the following bug fixes and improvements:

  • Restores the ability to view file names in the All Photos view in Photos
  • Restores the ability to filter by favorites, photos, videos, edited, and keywords in Days view in Photos
  • Fixes an issue where Messages would only send a single notification when the option to repeat alerts was enabled
  • Resolves an issue that caused Contacts to launch to the previously opened contact instead of the contact list
  • Adds a two-finger swipe gesture for back navigation in Apple News
  • Resolves issues that may occur in the Music app when displaying playlists inside folders and newly added songs in the Songs list
  • Improves reliability of migrating iTunes library databases into the Music, Podcasts, and TV apps
  • Fixes an issue where downloaded titles were not visible in the Downloads folder in the TV app

Enterprise content

  • When using the built-in keyboard with a non-U.S. keyboard layout, passwords with certain characters are no longer rejected at the Mac login window
  • When sign in with Apple ID is not allowed by a configuration profile, the Sign In button in System Preferences is now dimmed

macOS Catalina 10.15