diff --git a/ports/juce/avoid-macos-15-deprecations.patch b/ports/juce/avoid-macos-15-deprecations.patch
new file mode 100644
index 0000000000..30cf3b96be
--- /dev/null
+++ b/ports/juce/avoid-macos-15-deprecations.patch
@@ -0,0 +1,20 @@
+diff --git a/modules/juce_gui_basics/native/juce_PerScreenDisplayLinks_mac.h b/modules/juce_gui_basics/native/juce_PerScreenDisplayLinks_mac.h
+index 4562abf..8b1883b 100644
+--- a/modules/juce_gui_basics/native/juce_PerScreenDisplayLinks_mac.h
++++ b/modules/juce_gui_basics/native/juce_PerScreenDisplayLinks_mac.h
+@@ -23,6 +23,9 @@
+   ==============================================================================
+ */
+ 
++#pragma clang diagnostic push
++#pragma clang diagnostic ignored "-Wdeprecated-declarations"
++
+ namespace juce
+ {
+ 
+@@ -302,3 +305,5 @@ private:
+ };
+ 
+ } // namespace juce
++
++#pragma clang diagnostic pop
diff --git a/ports/juce/portfile.cmake b/ports/juce/portfile.cmake
index dd7f250f5b..4f142f6f47 100644
--- a/ports/juce/portfile.cmake
+++ b/ports/juce/portfile.cmake
@@ -16,6 +16,7 @@ vcpkg_from_github(
     missing-modules.diff
     prefer-cmake.diff
     vcpkg-compile-definitions.diff
+    avoid-macos-15-deprecations.patch
 )
 file(REMOVE_RECURSE "${SOURCE_PATH}/modules/juce_audio_devices/native/oboe")
 
diff --git a/ports/juce/vcpkg.json b/ports/juce/vcpkg.json
index 14beb51c94..bd27b6950c 100644
--- a/ports/juce/vcpkg.json
+++ b/ports/juce/vcpkg.json
@@ -2,7 +2,7 @@
   "$schema": "https://raw.githubusercontent.com/microsoft/vcpkg-tool/main/docs/vcpkg.schema.json",
   "name": "juce",
   "version": "8.0.4",
-  "port-version": 1,
+  "port-version": 2,
   "description": "Open-source cross-platform C++ application framework for desktop and mobile applications, including VST, VST3, AU, AUv3, AAX and LV2 audio plug-ins and plug-in hosts",
   "homepage": "https://juce.com",
   "license": null,
diff --git a/ports/msquic/avoid-w-invalid-unevaluated-string.patch b/ports/msquic/avoid-w-invalid-unevaluated-string.patch
new file mode 100644
index 0000000000..9ad0a24137
--- /dev/null
+++ b/ports/msquic/avoid-w-invalid-unevaluated-string.patch
@@ -0,0 +1,69 @@
+diff --git a/src/core/mtu_discovery.c b/src/core/mtu_discovery.c
+index a40c05c..8891efc 100644
+--- a/src/core/mtu_discovery.c
++++ b/src/core/mtu_discovery.c
+@@ -34,8 +34,8 @@ Abstract:
+ #include "mtu_discovery.c.clog.h"
+ #endif
+ 
+-CXPLAT_STATIC_ASSERT(CXPLAT_MAX_MTU >= QUIC_DPLPMTUD_DEFAULT_MAX_MTU, L"Default max must not be more than max");
+-CXPLAT_STATIC_ASSERT(QUIC_DPLPMTUD_MIN_MTU <= QUIC_DPLPMTUD_DEFAULT_MIN_MTU, L"Default min must not be less than min");
++CXPLAT_STATIC_ASSERT(CXPLAT_MAX_MTU >= QUIC_DPLPMTUD_DEFAULT_MAX_MTU, "Default max must not be more than max");
++CXPLAT_STATIC_ASSERT(QUIC_DPLPMTUD_MIN_MTU <= QUIC_DPLPMTUD_DEFAULT_MIN_MTU, "Default min must not be less than min");
+ 
+ _IRQL_requires_max_(PASSIVE_LEVEL)
+ static
+diff --git a/src/core/packet_builder.h b/src/core/packet_builder.h
+index 97d6079..912ce89 100644
+--- a/src/core/packet_builder.h
++++ b/src/core/packet_builder.h
+@@ -158,7 +158,7 @@ typedef struct QUIC_PACKET_BUILDER {
+ 
+ CXPLAT_STATIC_ASSERT(
+     sizeof(QUIC_PACKET_BUILDER) < 1024,
+-    L"Packet builder should be small enough to fit on the stack.");
++    "Packet builder should be small enough to fit on the stack.");
+ 
+ //
+ // Initializes the packet builder for general use.
+diff --git a/src/core/quicdef.h b/src/core/quicdef.h
+index 219ef33..07956b5 100644
+--- a/src/core/quicdef.h
++++ b/src/core/quicdef.h
+@@ -240,10 +240,10 @@ typedef struct QUIC_RX_PACKET QUIC_RX_PACKET;
+ #define QUIC_MAX_RANGE_ACK_PACKETS              0x800       // 2048
+ #define QUIC_MAX_RANGE_DECODE_ACKS              0x1000      // 4096
+ 
+-CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(QUIC_MAX_RANGE_ALLOC_SIZE), L"Must be power of two");
+-CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(QUIC_MAX_RANGE_DUPLICATE_PACKETS), L"Must be power of two");
+-CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(QUIC_MAX_RANGE_ACK_PACKETS), L"Must be power of two");
+-CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(QUIC_MAX_RANGE_DECODE_ACKS), L"Must be power of two");
++CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(QUIC_MAX_RANGE_ALLOC_SIZE), "Must be power of two");
++CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(QUIC_MAX_RANGE_DUPLICATE_PACKETS), "Must be power of two");
++CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(QUIC_MAX_RANGE_ACK_PACKETS), "Must be power of two");
++CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(QUIC_MAX_RANGE_DECODE_ACKS), "Must be power of two");
+ 
+ //
+ // Minimum MTU allowed to be configured. Must be able to fit a
+@@ -300,7 +300,7 @@ CXPLAT_STATIC_ASSERT(QUIC_INITIAL_PACKET_LENGTH >= QUIC_MIN_INITIAL_PACKET_LENGT
+ 
+ CXPLAT_STATIC_ASSERT(
+     QUIC_DEFAULT_DISCONNECT_TIMEOUT <= QUIC_MAX_DISCONNECT_TIMEOUT,
+-    L"Default disconnect timeout should always be less than max");
++    "Default disconnect timeout should always be less than max");
+ 
+ //
+ // The default connection idle timeout (in milliseconds).
+diff --git a/src/core/range.h b/src/core/range.h
+index b6d2cc0..ca6d3cd 100644
+--- a/src/core/range.h
++++ b/src/core/range.h
+@@ -21,7 +21,7 @@ typedef struct QUIC_SUBRANGE {
+ 
+ } QUIC_SUBRANGE;
+ 
+-CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(sizeof(QUIC_SUBRANGE)), L"Must be power of two");
++CXPLAT_STATIC_ASSERT(IS_POWER_OF_TWO(sizeof(QUIC_SUBRANGE)), "Must be power of two");
+ 
+ typedef struct QUIC_RANGE_SEARCH_KEY {
+ 
diff --git a/ports/msquic/portfile.cmake b/ports/msquic/portfile.cmake
index ef2bc1115d..c47cc177d9 100644
--- a/ports/msquic/portfile.cmake
+++ b/ports/msquic/portfile.cmake
@@ -16,6 +16,7 @@ vcpkg_from_github(
         uwp-link-libs.diff
         exports-for-msh3.diff
         no-werror.patch
+        avoid-w-invalid-unevaluated-string.patch
 )
 
 set(QUIC_TLS "schannel")
diff --git a/ports/msquic/vcpkg.json b/ports/msquic/vcpkg.json
index bcfe7039d9..216fc9f691 100644
--- a/ports/msquic/vcpkg.json
+++ b/ports/msquic/vcpkg.json
@@ -1,7 +1,7 @@
 {
   "name": "msquic",
   "version": "2.4.7",
-  "port-version": 2,
+  "port-version": 3,
   "description": "Cross-platform, C implementation of the IETF QUIC protocol",
   "homepage": "https://github.com/microsoft/msquic",
   "license": "MIT",
diff --git a/ports/qtbase/cmake/qt_install_submodule.cmake b/ports/qtbase/cmake/qt_install_submodule.cmake
index 8932256e2b..2f05a8b6f2 100644
--- a/ports/qtbase/cmake/qt_install_submodule.cmake
+++ b/ports/qtbase/cmake/qt_install_submodule.cmake
@@ -12,10 +12,6 @@ if(VCPKG_TARGET_IS_ANDROID AND NOT ANDROID_SDK_ROOT)
     message(FATAL_ERROR "${PORT} requires ANDROID_SDK_ROOT to be set. Consider adding it to the triplet." )
 endif()
 
-if(VCPKG_TARGET_IS_OSX AND (NOT VCPKG_OSX_DEPLOYMENT_TARGET OR VCPKG_OSX_DEPLOYMENT_TARGET VERSION_GREATER_EQUAL "15.0"))
-    message(WARNING "Qt6 does not yet cleanly support macOS 15.0, consider adding set(VCPKG_OSX_DEPLOYMENT_TARGET 14.0) or earlier to a custom triplet (https://learn.microsoft.com/en-us/vcpkg/users/examples/overlay-triplets-linux-dynamic#overriding-default-triplets).")
-endif()
-
 function(qt_download_submodule_impl)
     cmake_parse_arguments(PARSE_ARGV 0 "_qarg" "" "SUBMODULE" "PATCHES")
 
@@ -148,6 +144,10 @@ function(qt_cmake_configure)
         list(APPEND _qarg_OPTIONS "-DQT_MKSPECS_DIR:PATH=${CURRENT_HOST_INSTALLED_DIR}/share/Qt6/mkspecs")
     endif()
 
+    if(NOT DEFINED VCPKG_OSX_DEPLOYMENT_TARGET)
+        list(APPEND _qarg_OPTIONS "-DCMAKE_OSX_DEPLOYMENT_TARGET=14")
+    endif()
+
     vcpkg_cmake_configure(
         SOURCE_PATH "${SOURCE_PATH}"
         ${ninja_option}
diff --git a/ports/qtbase/vcpkg.json b/ports/qtbase/vcpkg.json
index b5a19e460c..f1381f933f 100644
--- a/ports/qtbase/vcpkg.json
+++ b/ports/qtbase/vcpkg.json
@@ -1,6 +1,7 @@
 {
   "name": "qtbase",
   "version": "6.8.2",
+  "port-version": 1,
   "description": "Qt Base (Core, Gui, Widgets, Network, ...)",
   "homepage": "https://www.qt.io/",
   "license": null,
diff --git a/scripts/azure-pipelines/azure-pipelines.yml b/scripts/azure-pipelines/azure-pipelines.yml
index 67190119dc..eaaaeea5e0 100644
--- a/scripts/azure-pipelines/azure-pipelines.yml
+++ b/scripts/azure-pipelines/azure-pipelines.yml
@@ -63,14 +63,14 @@ jobs:
 - template: osx/azure-pipelines.yml
   parameters:
     jobName: x64_osx
-    poolName: 'PrOsx-2024-07-12'
+    poolName: 'PrOsx-2025-01-24'
     vcpkgToolSha: ${{ parameters.vcpkgToolSha }}
     tripletPattern: ${{ parameters.tripletPattern }}
 
 - template: osx/azure-pipelines.yml
   parameters:
     jobName: arm64_osx
-    poolName: 'PrOsx-2024-07-12-arm64'
+    poolName: 'PrOsx-2025-01-24-arm64'
     vcpkgToolSha: ${{ parameters.vcpkgToolSha }}
     tripletPattern: ${{ parameters.tripletPattern }}
 
diff --git a/scripts/azure-pipelines/osx/README.md b/scripts/azure-pipelines/osx/README.md
index e51e15cf22..066631fc0f 100644
--- a/scripts/azure-pipelines/osx/README.md
+++ b/scripts/azure-pipelines/osx/README.md
@@ -23,60 +23,62 @@ This is the checklist for what the vcpkg team does when updating the macOS machi
 - [ ] Update or install parallels
 - [ ] Download the macOS installer from the app store. See https://support.apple.com/en-us/102662  
       Note: This portion of the instructions is that which breaks most often depending on what Parallels and macOS are doing.
-      You might need to use `softwareupdate --fetch-full-installer --full-installer-version 14.5` and point Parallels
+      You might need to use `softwareupdate --fetch-full-installer --full-installer-version 15.2` and point Parallels
       at that resulting installer in 'Applications' instead.
-- [ ] Run parallels, and select that installer you just downloaded. Name the VM "vcpkg-osx-<DATE>-amd64", for example "vcpkg-osx-2024-07-12-amd64".
+- [ ] Run parallels, and select that installer you just downloaded. Name the VM "vcpkg-osx-<DATE>-amd64", for example "vcpkg-osx-2025-01-24-amd64".
 - [ ] When creating the VM, customize the hardware to the following:
     * 12 processors
     * 24000 MB of memory
     * 350 GB disk
+    * Disable sound output
+    * Disable microphone
     * Do not share mac camera
 - [ ] Install MacOS like you would on real hardware.
     * Apple ID: 'Set Up Later' / Skip
     * Account name: vcpkg
     * A very similar password :)
+    * Don't enable Location Services
+    * Share crashes with app developers
     * Don't enable Ask Siri
 - [ ] Install Parallels Tools
 - [ ] Restart the VM
 - [ ] Change the desktop background to a solid color
 - [ ] Enable remote login in System Settings -> General -> Sharing -> Remote Login
-- [ ] Update the Azure Agent URI in setup-box.sh to the current version. You can find this by going to the agent pool, selecting "New agent", picking macOS, and copying the link. For example https://vstsagentpackage.azureedge.net/agent/3.241.0/vsts-agent-osx-x64-3.241.0.tar.gz
-- [ ] Start the VM. Change the screen resolution to not be teeny weeny eyestrain o vision.
+- [ ] Update the Azure Agent URI in setup-box.sh to the current version. You can find this by going to the agent pool, selecting "New agent", picking macOS, and copying the link. For example https://vstsagentpackage.azureedge.net/agent/4.248.0/vsts-agent-osx-x64-4.248.0.tar.gz
 - [ ] In the guest, set the vcpkg user to be able to use sudo without a password:
     ```sh
     printf 'vcpkg\tALL=(ALL)\tNOPASSWD:\tALL\n' | sudo tee -a '/etc/sudoers.d/vcpkg'
     sudo chmod 0440 '/etc/sudoers.d/vcpkg'
     ```
-- [ ] Copy setup-guest, setup-box.sh, and the xcode installer renamed to 'clt.dmg' to the host, and run setup-guest.sh. For example:
+- [ ] Copy setup-guest, setup-box.sh, and the xcode installer renamed to 'clt.dmg' to the host, and run setup-guest.sh.  From a developer machine:
     ```sh
-    scp ./setup-guest.sh vcpkg@MACHINE:/Users/vcpkg
-    scp ./setup-box.sh vcpkg@MACHINE:/Users/vcpkg
-    scp path/to/console/tools.dmg vcpkg@MACHINE:/Users/vcpkg/clt.dmg
-    ssh vcpkg@MACHINE
+    scp ./setup-guest.sh vcpkg@HOSTMACHINE:/Users/vcpkg
+    scp ./setup-box.sh vcpkg@HOSTMACHINE:/Users/vcpkg
+    scp path/to/console/tools.dmg vcpkg@HOSTMACHINE:/Users/vcpkg/clt.dmg
+    ssh vcpkg@HOSTMACHINE
     rm ~/.ssh/known_hosts
     chmod +x setup-guest.sh
     ./setup-guest.sh
     rm setup-guest.sh
     rm setup-box.sh
     rm clt.dmg
-    ```
-- [ ] In the guest, check that 'm4' works in the terminal. If it tries to reinstall the command line tools, let it do that. You might need to manually run this workaround from https://developer.apple.com/documentation/xcode-release-notes/xcode-15-release-notes#Known-Issues
-    ```sh
-    sudo mkdir -p /Library/Developer/CommandLineTools
-    sudo touch /Library/Developer/CommandLineTools/.beta
+    exit
     ```
 - [ ] Shut down the VM cleanly
+- [ ] Ensure that there is no host system specific 'hardware' like macOS install .isos attached.
 - [ ] Set the VM 'Isolated'
+- [ ] Boot and then cleanly shut down the VM.
 - [ ] In Parallels control center, right click the VM and select "Prepare for Transfer"
 - [ ] In Parallels control center, right click the VM and remove it, but "Keep Files"
 - [ ] Copy the packaged VM to Azure Storage, with something like:
     ```sh
-    ssh vcpkg@MACHINE
+    ssh vcpkg@HOSTMACHINE
     brew install azcopy
-    azcopy copy ~/Parallels/vcpkg-osx-2024-07-12-amd64.pvmp "https://vcpkgimageminting...../pvms?<SAS>"
-    azcopy copy ~/Parallels/vcpkg-osx-2024-07-12-amd64.sha256.txt "https://vcpkgimageminting...../pvms?<SAS>"
+    azcopy copy ~/Parallels/vcpkg-osx-2025-01-24-amd64.pvmp "https://vcpkgimageminting.blob.core.windows.net/pvms?<SAS>"
+    azcopy copy ~/Parallels/vcpkg-osx-2025-01-24-amd64.sha256.txt "https://vcpkgimageminting.blob.core.windows.net/pvms?<SAS>"
+    exit
     ```
-- [ ] Go to https://dev.azure.com/vcpkg/public/_settings/agentqueues and create a new self hosted Agent pool named `PrOsx-YYYY-MM-DD` based on the current date. Check 'Grant access permission to all pipelines.'
+- [ ] Go to https://dev.azure.com/vcpkg/public/_settings/agentqueues and create a new self hosted Agent pool named `PrOsx-YYYY-MM-DD` based on the current date. Grant microsoft.vcpkg.ci and microsoft.vcpkg.pr access.
 - [ ] Remove the macOS installer from Applications
 - [ ] Follow the "Deploying images" steps below for each machine in the fleet.
 
@@ -86,19 +88,21 @@ This is the checklist for what the vcpkg team does when updating the macOS machi
       and delete one of the agents that are idle.
 - [ ] Go to that machine in the KVM. (Passwords are stored as secrets in the CPP_GITHUB\vcpkg\vcpkgmm-passwords key vault)
 - [ ] Update the macos host
-- [ ] (Once only) install `macosvm` to `~` (this tarball is also backed up in our `vcpkg-image-minting` storage account):
+- [ ] (Once only) install `macosvm` to `~` (this tarball is also backed up in our `vcpkg-image-minting` storage account). For example from a dev workstation:
     ```sh
+    ssh vcpkg@HOSTMACHINE
     curl -L -o macosvm-0.2-1-arm64-darwin21.tar.gz https://github.com/s-u/macosvm/releases/download/0.2-1/macosvm-0.2-1-arm64-darwin21.tar.gz
     tar xvf macosvm-0.2-1-arm64-darwin21.tar.gz
     rm macosvm-0.2-1-arm64-darwin21.tar.gz
+    exit
     ```
-- [ ] Download the matching `.ipsw` for the macOS copy to install. See https://mrmacintosh.com/apple-silicon-m1-full-macos-restore-ipsw-firmware-files-database/ ; links there to find the .ipsw. Example: https://updates.cdn-apple.com/2024SpringFCS/fullrestores/062-01897/C874907B-9F82-4109-87EB-6B3C9BF1507D/UniversalMac_14.5_23F79_Restore.ipsw
-- [ ] Determine the VM name using the form "vcpkg-osx-<date>-arm64", for example "vcpkg-osx-2024-07-12-arm64".
-- [ ] Open a terminal and run the following commands to create the VM with vcpkg-osx-2024-07-12-arm64 and UniversalMac_14.5_23F79_Restore.ipsw replaced as appropriate.
+- [ ] Download the matching `.ipsw` for the macOS copy to install. See https://mrmacintosh.com/apple-silicon-m1-full-macos-restore-ipsw-firmware-files-database/ ; links there to find the .ipsw. Example: https://updates.cdn-apple.com/2024FallFCS/fullrestores/072-44245/E811A1B0-28A9-4FCD-AE32-322E796F0EB8/UniversalMac_15.2_24C101_Restore.ipsw
+- [ ] Determine the VM name using the form "vcpkg-osx-<date>-arm64", for example "vcpkg-osx-2025-01-24-arm64".
+- [ ] Open a terminal and run the following commands to create the VM with vcpkg-osx-2025-01-24-arm64 and UniversalMac_15.2_24C101_Restore.ipsw replaced as appropriate. This must be run in the KVM as it uses a GUI:
     ```sh
-    mkdir -p ~/Parallels/vcpkg-osx-2024-07-12-arm64
-    cd ~/Parallels/vcpkg-osx-2024-07-12-arm64
-    ~/macosvm --disk disk.img,size=500g --aux aux.img -c 8 -r 12g --restore ~/UniversalMac_14.5_23F79_Restore.ipsw ./vm.json
+    mkdir -p ~/Parallels/vcpkg-osx-2025-01-24-arm64
+    cd ~/Parallels/vcpkg-osx-2025-01-24-arm64
+    ~/macosvm --disk disk.img,size=500g --aux aux.img -c 8 -r 12g --restore ~/UniversalMac_15.2_24C101_Restore.ipsw ./vm.json
     ~/macosvm -g ./vm.json
     ```
 - [ ] Follow prompts as you would on real hardware.
@@ -109,43 +113,41 @@ This is the checklist for what the vcpkg team does when updating the macOS machi
     * Yes send crash reports
 - [ ] Set the desktop wallpaper to a fixed color from Settings -> Wallpaper . (This makes the KVM a lot easier to use :) )
 - [ ] Enable remote login in the VM: Settings -> General -> Sharing -> Remote Login
-- [ ] Set the vcpkg user to be able to use sudo without a password:
+- [ ] Set the vcpkg user to be able to use sudo without a password. For example from a dev workstation:
     ```sh
+    ssh vcpkg@HOSTMACHINE
+    rm ~/.ssh/known_hosts
     ssh vcpkg@vcpkgs-Virtual-Machine.local
     printf 'vcpkg\tALL=(ALL)\tNOPASSWD:\tALL\n' | sudo tee -a '/etc/sudoers.d/vcpkg'
     sudo chmod 0440 '/etc/sudoers.d/vcpkg'
     exit
     ```
-- [ ] Update the Azure Agent URI in setup-box.sh to the current version. You can find this by going to the agent pool, selecting "New agent", picking macOS, and copying the link. For example https://vstsagentpackage.azureedge.net/agent/3.241.0/vsts-agent-osx-arm64-3.241.0.tar.gz
+- [ ] Update the Azure Agent URI in setup-box.sh to the current version. You can find this by going to the agent pool, selecting "New agent", picking macOS, and copying the link. For example https://vstsagentpackage.azureedge.net/agent/4.248.0/vsts-agent-osx-arm64-4.248.0.tar.gz
 - [ ] Copy setup-box.sh and the xcode installer renamed to 'clt.dmg' to the host. For example from a dev workstation:
     ```sh
-    scp ./setup-guest.sh vcpkg@MACHINE:/Users/vcpkg
-    scp ./setup-box.sh vcpkg@MACHINE:/Users/vcpkg
-    scp path/to/console/tools.dmg vcpkg@MACHINE:/Users/vcpkg/clt.dmg
-    ssh vcpkg@MACHINE
+    scp ./setup-guest.sh vcpkg@HOSTMACHINE:/Users/vcpkg
+    scp ./setup-box.sh vcpkg@HOSTMACHINE:/Users/vcpkg
+    scp path/to/console/tools.dmg vcpkg@HOSTMACHINE:/Users/vcpkg/clt.dmg
+    ssh vcpkg@HOSTMACHINE
     chmod +x setup-guest.sh
-    rm ~/.ssh/known_hosts
     ./setup-guest.sh
     rm setup-guest.sh
     rm setup-box.sh
     rm clt.dmg
-    ```
-- [ ] In the guest, check that 'm4' works in the terminal. If it tries to reinstall the command line tools, let it do that. You might need to manually run this workaround from https://developer.apple.com/documentation/xcode-release-notes/xcode-15-release-notes#Known-Issues
-    ```sh
-    sudo mkdir -p /Library/Developer/CommandLineTools
-    sudo touch /Library/Developer/CommandLineTools/.beta
+    exit
     ```
 - [ ] Shut down the VM cleanly.
 - [ ] Mint a SAS token to vcpkgimageminting/pvms with read, add, create, write, and list permissions.
-- [ ] Open a terminal on the host and package the VM into a tarball:
+- [ ] Package the VM into a tarball. For example from a dev workstation:
     ```sh
+    ssh vcpkg@HOSTMACHINE
     cd ~/Parallels
     aa archive -d vcpkg-osx-<date>-arm64 -o vcpkg-osx-<date>-arm64.aar -enable-holes
     brew install azcopy
     azcopy copy vcpkg-osx-<date>-arm64.aar "https://vcpkgimageminting.blob.core.windows.net/pvms?<SAS>"
-    rm *.aar
+    exit
     ```
-- [ ] Go to https://dev.azure.com/vcpkg/public/_settings/agentqueues and create a new self hosted Agent pool named `PrOsx-YYYY-MM-DD-arm64` based on the current date. Check 'Grant access permission to all pipelines.'
+- [ ] Go to https://dev.azure.com/vcpkg/public/_settings/agentqueues and create a new self hosted Agent pool named `PrOsx-YYYY-MM-DD-arm64` based on the current date. Grant microsoft.vcpkg.ci and microsoft.vcpkg.pr access.
 - [ ] Follow the "Deploying images" steps below for each machine in the fleet.
 
 ## Deploying images
@@ -158,30 +160,41 @@ Run these steps on each machine to add to the fleet. Skip steps that were done i
 - [ ] Log in to the machine using the KVM.
 - [ ] Check for software updates in macOS system settings
 - [ ] Check for software updates in Parallels' UI
-- [ ] Mint a SAS token URI to the box to use from the Azure portal if you don't already have one, and download the VM. (Recommend running this via SSH from domain joined machine due to containing SAS tokens)
+- [ ] Mint a SAS token URI to the box to use from the Azure portal if you don't already have one, and download the VM. (Recommend running this via SSH from domain joined machine due to containing SAS tokens). From a developer machine:
     ```sh
+    ssh vcpkg@HOSTMACHINE
     brew install azcopy
     cd ~/Parallels
     azcopy copy "https://vcpkgimageminting.blob.core.windows.net/pvms/vcpkg-osx-<DATE>-amd64.pvmp?<SAS>" .
     azcopy copy "https://vcpkgimageminting.blob.core.windows.net/pvms/vcpkg-osx-<DATE>-amd64.sha256.txt?<SAS>" .
+    exit
     ```
 - [ ] Open the .pvmp in Parallels, and unpack it.
-- [ ] Start the VM
+- [ ] Open the 'Configure' screen for the VM, and under Options -> Startup and Shutdown, set the following:
+    * Custom
+    * Start Automatically: When Mac Starts
+    * Startup View: Headless
+    * On VM Shutdown: Close Window (this one should already be set)
+    * On Mac Shutdown: Shut Down
+    * On Window Close: Keep Running in the Background
+- [ ] Close and restart Parallels Desktop. The VM should start automatically.
 - [ ] [grab a PAT][] if you don't already have one
-- [ ] Copy the guest deploy script to the host, and run it with a first parameter of your PAT
+- [ ] Copy the guest deploy script to the host, and run it with a first parameter of your PAT. From a developer machine:
     ```sh
-    scp ./register-guest.sh vcpkg@MACHINE:/Users/vcpkg
-    ssh vcpkg@MACHINE
-    rm ~/.ssh/known_hosts
-    chmod +x /Users/vcpkg/register-guest.sh
-    /Users/vcpkg/register-guest.sh <PAT>
+    scp ./register-guest.sh vcpkg@HOSTMACHINE:/Users/vcpkg
+    ssh vcpkg@HOSTMACHINE
+    rm .ssh/known_hosts
+    chmod +x register-guest.sh
+    ./register-guest.sh <PAT>
+    rm register-guest.sh
+    exit
     ```
-- [ ] Open a terminal window on the host and run the agent
+- [ ] In the VM, open a terminal on the host and run:
     ```
     ssh -i ~/Parallels/*/id_guest vcpkg@`prlctl list --full | sed -nr 's/^.*running *([0-9]{1,3}\.[0-9]{1,3}\.[0-9]{1,3}\.[0-9]{1,3}).*/\1/p'`
     ~/myagent/run.sh
     ```
-- [ ] Check that the machine shows up in the pool, and lock the vcpkg user on the host.
+- [ ] Check that the machine shows up in the pool.
 - [ ] Lock the screen on the host.
 - [ ] Update the "vcpkg Macs" spreadsheet line for the machine with the new pool.
 
@@ -194,18 +207,23 @@ Run these steps on each machine to add to the fleet. Skip steps that were done i
 - [ ] If this machine was used before, delete it from the pool of which it is a member from https://dev.azure.com/vcpkg/public/_settings/agentqueues
 - [ ] Log in to the machine using the KVM.
 - [ ] Check for software updates in macOS system settings
-- [ ] (Once only) install `macosvm` to `~` (this tarball is also backed up in our `vcpkg-image-minting` storage account):
+- [ ] (Once only) install `macosvm` to `~` (this tarball is also backed up in our `vcpkg-image-minting` storage account). From a developer machine:
     ```sh
+    ssh vcpkg@HOSTMACHINE
     curl -L -o macosvm-0.2-1-arm64-darwin21.tar.gz https://github.com/s-u/macosvm/releases/download/0.2-1/macosvm-0.2-1-arm64-darwin21.tar.gz
     tar xvf macosvm-0.2-1-arm64-darwin21.tar.gz
     rm macosvm-0.2-1-arm64-darwin21.tar.gz
+    exit
     ```
-- [ ] Skip if this is the image building machine. Mint a SAS token URI to the box to use from the Azure portal if you don't already have one, and download the VM. (Recommend running this via SSH from domain joined machine due to containing SAS tokens)
+- [ ] Skip if this is the image building machine. Mint a SAS token URI to the box to use from the Azure portal if you don't already have one, and download the VM. (Recommend running this via SSH from domain joined machine due to containing SAS tokens). From a developer machine:
     ```sh
+    ssh vcpkg@HOSTMACHINE
+    brew install azcopy
     mkdir -p ~/Parallels
     cd ~/Parallels
     azcopy copy "https://vcpkgimageminting.blob.core.windows.net/pvms/vcpkg-osx-<DATE>-arm64.aar?<SAS>" vcpkg-osx-<DATE>-arm64.aar
     aa extract -d vcpkg-osx-<DATE>-arm64 -i ./vcpkg-osx-<DATE>-arm64.aar -enable-holes
+    exit
     ```
 - [ ] Open a separate terminal window on the host and start the VM by running:
     ```sh
@@ -215,9 +233,9 @@ Run these steps on each machine to add to the fleet. Skip steps that were done i
 - [ ] [grab a PAT][] if you don't already have one
 - [ ] Copy the guest deploy script to the host, and run it with a first parameter of your PAT. From a developer machine:
     ```sh
-    scp ./register-guest.sh vcpkg@MACHINE:/Users/vcpkg
-    ssh vcpkg@MACHINE
-    rm ~/.ssh/known_hosts
+    scp ./register-guest.sh vcpkg@HOSTMACHINE:/Users/vcpkg
+    ssh vcpkg@HOSTMACHINE
+    rm .ssh/known_hosts
     chmod +x register-guest.sh
     ./register-guest.sh <PAT>
     rm register-guest.sh
diff --git a/scripts/azure-pipelines/osx/setup-box.sh b/scripts/azure-pipelines/osx/setup-box.sh
index 1a23a8b8b4..3beb8838f7 100644
--- a/scripts/azure-pipelines/osx/setup-box.sh
+++ b/scripts/azure-pipelines/osx/setup-box.sh
@@ -16,12 +16,12 @@ else
     (echo; echo 'eval "$(/usr/local/bin/brew shellenv)"') >> /Users/vcpkg/.zprofile
     eval "$(/usr/local/bin/brew shellenv)"
 fi
-brew install autoconf-archive autoconf automake azure-cli bison cmake gettext gfortran gperf gtk-doc libtool meson mono nasm ninja pkg-config powershell python-setuptools texinfo yasm
+brew install autoconf-archive autoconf automake azure-cli bison cmake gettext gfortran gnu-sed gperf gtk-doc libtool meson mono nasm ninja pkg-config powershell python-setuptools texinfo yasm
 mkdir ~/Data
 if [ `uname -m` = 'arm64' ]; then
-curl -s -o ~/Downloads/azure-agent.tar.gz https://vstsagentpackage.azureedge.net/agent/3.241.0/vsts-agent-osx-arm64-3.241.0.tar.gz
+curl -s -o ~/Downloads/azure-agent.tar.gz https://vstsagentpackage.azureedge.net/agent/4.248.0/vsts-agent-osx-arm64-4.248.0.tar.gz
 else
-curl -s -o ~/Downloads/azure-agent.tar.gz https://vstsagentpackage.azureedge.net/agent/3.241.0/vsts-agent-osx-x64-3.241.0.tar.gz
+curl -s -o ~/Downloads/azure-agent.tar.gz https://vstsagentpackage.azureedge.net/agent/4.248.0/vsts-agent-osx-x64-4.248.0.tar.gz
 fi
 mkdir ~/myagent
 tar xf ~/Downloads/azure-agent.tar.gz -C ~/myagent
diff --git a/scripts/ci.baseline.txt b/scripts/ci.baseline.txt
index b9e3d36d80..f0eeedc4e1 100644
--- a/scripts/ci.baseline.txt
+++ b/scripts/ci.baseline.txt
@@ -46,6 +46,7 @@ ace:x64-android=fail
 allegro5:arm-neon-android=fail
 allegro5:arm64-android=fail
 allegro5:x64-android=fail
+angelscript:x64-osx=fail
 apr:arm-neon-android=fail
 apr:arm64-android=fail
 apr:x64-android=fail
@@ -62,8 +63,6 @@ azure-identity-cpp:x64-android=fail
 # C++20 conformant compiler required
 atliac-minitest:x64-linux=fail
 atliac-minitest:arm64-uwp=fail
-atliac-minitest:arm64-osx=fail
-atliac-minitest:x64-osx=fail
 atliac-minitest:x64-uwp=fail
 backward-cpp:arm-neon-android=fail
 backward-cpp:arm64-android=fail
@@ -350,6 +349,8 @@ freeglut:x64-android=fail
 # Needs XQuartz
 freeglut:x64-osx=fail
 freeglut:arm64-osx=fail
+freerdp:arm64-osx=fail
+freerdp:x64-osx=fail
 fruit:arm-neon-android=fail
 fruit:arm64-android=fail
 fruit:x64-android=fail
@@ -521,8 +522,6 @@ libcaer:x64-android=fail
 libcanberra:arm-neon-android=fail
 libcanberra:arm64-android=fail
 libcanberra:x64-android=fail
-libcoro:x64-osx=fail
-libcoro:arm64-osx=fail
 libcpplocate:arm-neon-android=fail
 libcpplocate:arm64-android=fail
 libcpplocate:x64-android=fail
@@ -784,9 +783,6 @@ nrf-ble-driver:arm64-android=fail
 nrf-ble-driver:x64-android=fail
 nvtt:x64-android=fail
 oatpp-libressl:x64-android=fail
-# needs gnu-sed
-octave:arm64-osx=fail
-octave:x64-osx=fail
 ode:arm64-windows=fail
 ode:arm64-windows-static-md=fail
 offscale-libetcd-cpp:arm64-uwp=fail
@@ -1136,6 +1132,7 @@ torch-th:x64-windows-static=fail
 tvision:arm-neon-android=fail
 tvision:arm64-android=fail
 tvision:x64-android=fail
+urho3d:x64-osx=fail
 # Proper support for a true static usd build is left as a future port improvement. It probably require fiddling with its monolithic mode.
 usd:x64-windows-static=skip
 # needs android-24
@@ -1206,13 +1203,14 @@ zyre:arm64-windows-static-md=fail
 zyre:x64-windows-static-md=fail
 
 # Ports which needs to pass in CI
-cmake:x64-windows=pass
-cmake:x64-windows-static=pass
-cmake:x64-windows-static-md=pass
-cmake:arm64-windows=pass
+cmake:arm64-osx=pass
 cmake:arm64-windows-static-md=pass
+cmake:arm64-windows=pass
 cmake:x64-linux=pass
 cmake:x64-osx=pass
+cmake:x64-windows-static-md=pass
+cmake:x64-windows-static=pass
+cmake:x64-windows=pass
 cmake-user:arm64-uwp=pass
 cmake-user:arm64-windows=pass
 cmake-user:arm64-windows-static-md=pass
@@ -1286,7 +1284,6 @@ vcpkg-ci-freerdp:arm-neon-android=pass
 vcpkg-ci-freerdp:arm64-android=pass
 vcpkg-ci-freerdp:x64-android=pass
 vcpkg-ci-freerdp:x64-linux=pass
-vcpkg-ci-freerdp:x64-osx=pass
 vcpkg-ci-freerdp:x64-windows-static-md=pass
 vcpkg-ci-freerdp:x64-windows-static=pass
 vcpkg-ci-freerdp:x64-windows=pass
@@ -1333,12 +1330,13 @@ vcpkg-ci-opencv:x64-windows-static-md=pass
 vcpkg-ci-opencv:x64-windows-static=pass
 vcpkg-ci-opencv:x64-windows=pass
 vcpkg-ci-opencv:x86-windows=pass
-vcpkg-ci-openimageio:x86-windows=pass
-vcpkg-ci-openimageio:x64-windows=pass
-vcpkg-ci-openimageio:x64-windows-static=pass
-vcpkg-ci-openimageio:x64-windows-static-md=pass
-vcpkg-ci-openimageio:x64-osx=pass
+vcpkg-ci-openimageio:arm64-osx=pass
 vcpkg-ci-openimageio:x64-linux=pass
+vcpkg-ci-openimageio:x64-osx=pass
+vcpkg-ci-openimageio:x64-windows-static-md=pass
+vcpkg-ci-openimageio:x64-windows-static=pass
+vcpkg-ci-openimageio:x64-windows=pass
+vcpkg-ci-openimageio:x86-windows=pass
 vcpkg-ci-paraview:x64-linux=pass
 vcpkg-ci-paraview:x64-osx=pass
 vcpkg-ci-paraview:arm64-osx=pass
diff --git a/versions/baseline.json b/versions/baseline.json
index 43ae118e4a..dd280fcf2e 100644
--- a/versions/baseline.json
+++ b/versions/baseline.json
@@ -3898,7 +3898,7 @@
     },
     "juce": {
       "baseline": "8.0.4",
-      "port-version": 1
+      "port-version": 2
     },
     "jwt-cpp": {
       "baseline": "0.7.0",
@@ -6190,7 +6190,7 @@
     },
     "msquic": {
       "baseline": "2.4.7",
-      "port-version": 2
+      "port-version": 3
     },
     "mstch": {
       "baseline": "1.0.2",
@@ -7586,7 +7586,7 @@
     },
     "qtbase": {
       "baseline": "6.8.2",
-      "port-version": 0
+      "port-version": 1
     },
     "qtcharts": {
       "baseline": "6.8.2",
diff --git a/versions/j-/juce.json b/versions/j-/juce.json
index 1f164870d8..9215226c02 100644
--- a/versions/j-/juce.json
+++ b/versions/j-/juce.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "0a2790a3140e51910cc6ac4846aea3f1243a62bd",
+      "version": "8.0.4",
+      "port-version": 2
+    },
     {
       "git-tree": "e35480f559031fb4b98bfa887ebf88291183a6ea",
       "version": "8.0.4",
diff --git a/versions/m-/msquic.json b/versions/m-/msquic.json
index 86d7e71216..919742d933 100644
--- a/versions/m-/msquic.json
+++ b/versions/m-/msquic.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "4e5648681b1e1f2ac74e7ab7be04d1215a0063bf",
+      "version": "2.4.7",
+      "port-version": 3
+    },
     {
       "git-tree": "7b56cfbd638c6711b76cab27d5f9a71f17341d36",
       "version": "2.4.7",
diff --git a/versions/q-/qtbase.json b/versions/q-/qtbase.json
index 4ca3d10a5c..2793d66702 100644
--- a/versions/q-/qtbase.json
+++ b/versions/q-/qtbase.json
@@ -1,5 +1,10 @@
 {
   "versions": [
+    {
+      "git-tree": "744273bb84e2107bb024f6d32e5c03890b4c4f2d",
+      "version": "6.8.2",
+      "port-version": 1
+    },
     {
       "git-tree": "f3ba3628279d2cc0b50125dbbae1193d329f89d0",
       "version": "6.8.2",