diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index c071a11..5da2416 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -10,22 +10,17 @@ jobs:
   build:
     name: Build
     runs-on: ubuntu-latest
-    strategy:
-      matrix:
-        ubuntu-version:
-        - 22.04
-        - 24.04
     steps:
       - uses: actions/checkout@v6
-      - run: make UBUNTU=${{ matrix.ubuntu-version }} update
-      - run: make UBUNTU=${{ matrix.ubuntu-version }} build
+      - run: make DEBIAN=trixie update
+      - run: make DEBIAN=trixie build
       - name: Log in to docker
         uses: docker/login-action@v3
         with:
           username: ${{ secrets.DOCKER_USERNAME }}
           password: ${{ secrets.DOCKER_PASSWORD }}
         if: ${{ github.repository_owner == 'wpilibsuite' && github.ref == 'refs/heads/main' }}
-      - run: make UBUNTU=${{ matrix.ubuntu-version }} push
+      - run: make DEBIAN=trixie push
         if: ${{ github.repository_owner == 'wpilibsuite' && github.ref == 'refs/heads/main' }}
 
   build-ds:
@@ -66,7 +61,7 @@ jobs:
     strategy:
       matrix:
         debian-version:
-        - bookworm
+        - trixie
     steps:
       - uses: actions/checkout@v6
       - run: make DEBIAN=${{ matrix.debian-version }} update/arm
@@ -77,47 +72,30 @@ jobs:
           username: ${{ secrets.DOCKER_USERNAME }}
           password: ${{ secrets.DOCKER_PASSWORD }}
         if: ${{ github.repository_owner == 'wpilibsuite' && github.ref == 'refs/heads/main' }}
-      - run: make UBUNTU=${{ matrix.debian-version }} push/arm-base
+      - run: make DEBIAN=${{ matrix.debian-version }} push/arm-base
         if: ${{ github.repository_owner == 'wpilibsuite' && github.ref == 'refs/heads/main' }}
 
   build-minimal:
     name: Build Minimal
     runs-on: ubuntu-latest
-    strategy:
-      matrix:
-        ubuntu-version:
-        - 22.04
-        - 24.04
     steps:
       - uses: actions/checkout@v6
-      - run: make UBUNTU=${{ matrix.ubuntu-version }} update
-      - run: make UBUNTU=${{ matrix.ubuntu-version }} build/minimal-cross
+      - run: make DEBIAN=trixie update
+      - run: make DEBIAN=trixie build/minimal-cross
       - name: Log in to docker
         uses: docker/login-action@v3
         with:
           username: ${{ secrets.DOCKER_USERNAME }}
           password: ${{ secrets.DOCKER_PASSWORD }}
         if: ${{ github.repository_owner == 'wpilibsuite' && github.ref == 'refs/heads/main' }}
-      - run: make UBUNTU=${{ matrix.ubuntu-version }} push/minimal-cross
+      - run: make DEBIAN=trixie push/minimal-cross
         if: ${{ github.repository_owner == 'wpilibsuite' && github.ref == 'refs/heads/main' }}
 
-      - run: make UBUNTU=${{ matrix.ubuntu-version }} save/minimal-cross
-      - name: Upload roborio cross base image
-        uses: actions/upload-artifact@v7
-        with:
-          name: roborio-${{ matrix.ubuntu-version }}
-          path: roborio.tar.zst
-          retention-days: 1
-      - name: Upload raspbian cross base image
-        uses: actions/upload-artifact@v7
-        with:
-          name: raspbian-${{ matrix.ubuntu-version }}
-          path: raspbian.tar.zst
-          retention-days: 1
+      - run: make DEBIAN=trixie save/minimal-cross
       - name: Upload systemcore cross base image
         uses: actions/upload-artifact@v7
         with:
-          name: systemcore-${{ matrix.ubuntu-version }}
+          name: systemcore-trixie
           path: systemcore.tar.zst
           retention-days: 1
 
@@ -128,28 +106,12 @@ jobs:
     strategy:
       matrix:
         type:
-        - raspbian
+        - systemcore
         pyversion:
-        - py311
-        - py312
         - py313
         - py314
-        ubuntu-version:
-        - 22.04
-        - 24.04
-        include:
-        - type: roborio
-          pyversion: py313
-          ubuntu-version: 22.04
-        - type: roborio
-          pyversion: py314
-          ubuntu-version: 22.04
-        - type: systemcore
-          pyversion: py313
-          ubuntu-version: 24.04
-        - type: systemcore
-          pyversion: py314
-          ubuntu-version: 24.04
+        debian-version:
+        - trixie
 
     steps:
     - uses: actions/checkout@v6
@@ -157,7 +119,7 @@ jobs:
     - name: Download image
       uses: actions/download-artifact@v4
       with:
-        name: ${{ matrix.type }}-${{ matrix.ubuntu-version }}
+        name: ${{ matrix.type }}-${{ matrix.debian-version }}
         path: img
 
     - name: Load image
@@ -166,7 +128,7 @@ jobs:
         rm img/${{ matrix.type }}.tar.zst
 
     - name: Build image
-      run: make UBUNTU=${{ matrix.ubuntu-version }} build/cross-${{ matrix.type }}-${{ matrix.pyversion }}
+      run: make DEBIAN=trixie build/cross-${{ matrix.type }}-${{ matrix.pyversion }}
     - name: Log in to docker
       uses: docker/login-action@v3
       with:
@@ -174,5 +136,5 @@ jobs:
         password: ${{ secrets.DOCKER_PASSWORD }}
       if: ${{ github.repository_owner == 'wpilibsuite' && github.ref == 'refs/heads/main' }}
     - name: Upload image
-      run: make UBUNTU=${{ matrix.ubuntu-version }} push/cross-${{ matrix.type }}-${{ matrix.pyversion }}
+      run: make DEBIAN=trixie push/cross-${{ matrix.type }}-${{ matrix.pyversion }}
       if: ${{ github.repository_owner == 'wpilibsuite' && github.ref == 'refs/heads/main' }}
diff --git a/Makefile b/Makefile
index 33e4f63..956c894 100644
--- a/Makefile
+++ b/Makefile
@@ -1,6 +1,5 @@
-UBUNTU?=22.04
 OPENSDK_UBUNTU?=22.04
-DEBIAN?=bookworm
+DEBIAN?=trixie
 
 DS?=trixie
 
@@ -13,7 +12,7 @@ usage:
 	@echo "Run make update, make build, and make push"
 
 update:
-	docker pull docker.io/ubuntu:${UBUNTU}
+	docker pull docker.io/debian:${DEBIAN}
 	docker pull docker.io/ubuntu:${OPENSDK_UBUNTU}
 
 update/arm:
@@ -23,37 +22,27 @@ build: build/base build/cross build/opensdk
 
 build/arm-base:
 	cd debian-base && \
-		docker build -t ${DOCKER_USER}/debian-base:arm64-${DEBIAN} -f Dockerfile.${DEBIAN} .
+		docker build -t ${DOCKER_USER}/debian-base:arm64-${DEBIAN} -f Dockerfile.arm64.${DEBIAN} .
 
 build/base:
-	cd ubuntu-base && \
-		docker build -t ${DOCKER_USER}/ubuntu-base:${UBUNTU} -f Dockerfile.${UBUNTU} .
+	cd debian-base && \
+		docker build -t ${DOCKER_USER}/debian-base:${DEBIAN} -f Dockerfile.x64.${DEBIAN} .
 
 build/cross: build/base
-	cd roborio-cross-ubuntu && \
-	    docker build -t ${DOCKER_USER}/roborio-cross-ubuntu:2025-${UBUNTU} -f Dockerfile.2025 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=base .
-	cd systemcore-cross-ubuntu && \
-	    docker build -t ${DOCKER_USER}/systemcore-cross-ubuntu:2027-${UBUNTU} -f Dockerfile.2027 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=base .
-	cd raspbian-cross-ubuntu && \
-	    docker build -t ${DOCKER_USER}/raspbian-cross-ubuntu:bookworm-${UBUNTU} -f Dockerfile.bookworm-2025 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=base . && \
-	    docker build -t ${DOCKER_USER}/raspbian-cross-ubuntu:2027-bookworm-${UBUNTU} -f Dockerfile.bookworm-2027 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=base .
-	cd aarch64-cross-ubuntu && \
-	    docker build -t ${DOCKER_USER}/aarch64-cross-ubuntu:bookworm-${UBUNTU} -f Dockerfile.bookworm-2025 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=base . && \
-	    docker build -t ${DOCKER_USER}/aarch64-cross-ubuntu:2027-bookworm-${UBUNTU} -f Dockerfile.bookworm-2027 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=base .
+	cd systemcore-cross-debian && \
+	    docker build -t ${DOCKER_USER}/systemcore-cross-debian:${DEBIAN} -f Dockerfile.${DEBIAN} --build-arg DEBIAN=${DEBIAN} --build-arg TYPE=base .
+	cd aarch64-cross-debian && \
+	    docker build -t ${DOCKER_USER}/aarch64-cross-debian:${DEBIAN} -f Dockerfile.${DEBIAN} --build-arg DEBIAN=${DEBIAN} --build-arg TYPE=base .
 
 build/minimal-base:
-	cd ubuntu-minimal-base && \
-		docker build -t ${DOCKER_USER}/ubuntu-minimal-base:${UBUNTU} -f Dockerfile.${UBUNTU} .
+	cd debian-minimal-base && \
+		docker build -t ${DOCKER_USER}/debian-minimal-base:${DEBIAN} -f Dockerfile.${DEBIAN} .
 
 build/minimal-cross: build/minimal-base
-	cd roborio-cross-ubuntu && \
-	    docker build -t ${DOCKER_USER}/roborio-cross-ubuntu-minimal:2025-${UBUNTU} -f Dockerfile.2025 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=minimal-base .
-	cd systemcore-cross-ubuntu && \
-	    docker build -t ${DOCKER_USER}/systemcore-cross-ubuntu-minimal:2027-${UBUNTU} -f Dockerfile.2027 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=minimal-base .
-	cd raspbian-cross-ubuntu && \
-	    docker build -t ${DOCKER_USER}/raspbian-cross-ubuntu-minimal:bookworm-${UBUNTU} -f Dockerfile.bookworm-2025 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=minimal-base .
-	cd aarch64-cross-ubuntu && \
-	    docker build -t ${DOCKER_USER}/aarch64-cross-ubuntu-minimal:bookworm-${UBUNTU} -f Dockerfile.bookworm-2025 --build-arg UBUNTU=${UBUNTU} --build-arg TYPE=minimal-base .
+	cd systemcore-cross-debian && \
+	    docker build -t ${DOCKER_USER}/systemcore-cross-debian-minimal:${DEBIAN} -f Dockerfile.${DEBIAN} --build-arg DEBIAN=${DEBIAN} --build-arg TYPE=minimal-base .
+	cd aarch64-cross-debian && \
+	    docker build -t ${DOCKER_USER}/aarch64-cross-debian-minimal:${DEBIAN} -f Dockerfile.${DEBIAN} --build-arg DEBIAN=${DEBIAN} --build-arg TYPE=minimal-base .
 
 build/opensdk:
 	cd opensdk/ubuntu && \
@@ -65,24 +54,18 @@ push/arm-base:
 	docker push ${DOCKER_USER}/debian-base:arm64-${DEBIAN}
 
 push/base:
-	docker push ${DOCKER_USER}/ubuntu-base:${UBUNTU}
+	docker push ${DOCKER_USER}/debian-base:${DEBIAN}
 
 push/cross: push/base
-	docker push ${DOCKER_USER}/roborio-cross-ubuntu:2025-${UBUNTU}
-	docker push ${DOCKER_USER}/systemcore-cross-ubuntu:2027-${UBUNTU}
-	docker push ${DOCKER_USER}/raspbian-cross-ubuntu:bookworm-${UBUNTU}
-	docker push ${DOCKER_USER}/aarch64-cross-ubuntu:bookworm-${UBUNTU}
-	docker push ${DOCKER_USER}/raspbian-cross-ubuntu:2027-bookworm-${UBUNTU}
-	docker push ${DOCKER_USER}/aarch64-cross-ubuntu:2027-bookworm-${UBUNTU}
+	docker push ${DOCKER_USER}/systemcore-cross-debian:${DEBIAN}
+	docker push ${DOCKER_USER}/aarch64-cross-debian:${DEBIAN}
 
 push/minimal-base:
-	docker push ${DOCKER_USER}/ubuntu-minimal-base:${UBUNTU}
+	docker push ${DOCKER_USER}/debian-minimal-base:${DEBIAN}
 
 push/minimal-cross: push/minimal-base
-	docker push ${DOCKER_USER}/roborio-cross-ubuntu-minimal:2025-${UBUNTU}
-	docker push ${DOCKER_USER}/systemcore-cross-ubuntu-minimal:2027-${UBUNTU}
-	docker push ${DOCKER_USER}/raspbian-cross-ubuntu-minimal:bookworm-${UBUNTU}
-	docker push ${DOCKER_USER}/aarch64-cross-ubuntu-minimal:bookworm-${UBUNTU}
+	docker push ${DOCKER_USER}/systemcore-cross-debian-minimal:${DEBIAN}
+	docker push ${DOCKER_USER}/aarch64-cross-debian-minimal:${DEBIAN}
 
 push/opensdk:
 	docker push ${DOCKER_USER}/opensdk-ubuntu:${OPENSDK_UBUNTU}
@@ -90,11 +73,9 @@ push/opensdk:
 
 .PHONY: save/minimal-cross
 save/minimal-cross:
-	docker save ${DOCKER_USER}/roborio-cross-ubuntu-minimal:2025-${UBUNTU} | zstd > roborio.tar.zst
-	docker save ${DOCKER_USER}/systemcore-cross-ubuntu-minimal:2027-${UBUNTU} | zstd > systemcore.tar.zst
-	docker save ${DOCKER_USER}/raspbian-cross-ubuntu-minimal:bookworm-${UBUNTU} | zstd > raspbian.tar.zst
+	docker save ${DOCKER_USER}/systemcore-cross-debian-minimal:${DEBIAN} | zstd > systemcore.tar.zst
 
-include cross-ubuntu-py/py.mk
+include cross-debian-py/py.mk
 
 update/ds:
 	docker pull docker.io/debian:${DS}
diff --git a/README.md b/README.md
index 08332fa..59ccb09 100644
--- a/README.md
+++ b/README.md
@@ -3,47 +3,42 @@ Docker images for building WPILib
 
 These are the dockerfiles for the wpilib dockerhub repositories.
 
-ubuntu-base
- - Based on official ubuntu repo (host)
+debian-base
+ - Based on official debian repo (host)
  - Contains Java and C++ native tools required for WPILib development
  - Base image for cross-compiler images
- - Published as wpilib/ubuntu-base:host ubuntu version (e.g. 18.04)
+ - Published as wpilib/debian-base:arch-host debian codename (e.g. trixie or arm64-trixie)
 
-ubuntu-minimal-base
- - Based on official ubuntu repo (host)
+debian-minimal-base
+ - Based on official debian repo (host)
  - Base image for minimal cross-compiler images that only contain cross compiler
- - Published as wpilib/ubuntu-minimal-base:host ubuntu version (e.g. 18.04)
-
-roborio-cross-ubuntu
- - Based on wpilib/ubuntu-base
- - Cross-compiler for roboRIO
- - Published as wpilib/roborio-cross-ubuntu:frc season-host ubuntu version
-   (e.g. 2020-18.04)
- - Minimal variant published as roborio-cross-ubuntu-minimal
-
-systemcore-cross-ubuntu
- - Based on wpilib/ubuntu-base
- - Cross-compiler for systemcore (Bookworm for now)
- - Published as wpilib/systemcore-cross-ubuntu:frc season-host ubuntu version
-   (e.g. 2020-18.04)
- - Minimal variant published as systemcore-cross-ubuntu-minimal
-
-raspbian-cross-ubuntu
- - Based on wpilib/ubuntu-base
- - Cross-compiler for Raspbian
- - Published as wpilib/raspbian-cross-ubuntu:target version-host ubuntu version
-   (e.g. 10-18.04)
- - Minimal variant published as raspbian-cross-ubuntu-minimal
-
-aarch64-cross-ubuntu
- - Based on wpilib/ubuntu-base
+ - Published as wpilib/debian-minimal-base:host debian codename (e.g. trixie)
+
+driverstation-base
+ - Based on official debian repo (host)
+ - Base image for building the Driver Station application
+ - Published as wpilib/driverstation-base:arch (e.g. x64 or arm64)
+
+opensdk-ubuntu
+ - Based on official ubuntu repo (host)
+ - Base image for building opensdk toolchains
+ - Published as wpilib/opensdk-ubuntu:host ubuntu version (e.g. 24.04)
+
+systemcore-cross-debian
+ - Based on wpilib/debian-base
+ - Cross-compiler for systemcore (Trixie for now)
+ - Published as wpilib/systemcore-cross-debian:host debian codename
+   (e.g. trixie)
+ - Minimal variant published as wpilib/systemcore-cross-debian-minimal
+
+aarch64-cross-debian
+ - Based on wpilib/debian-base
  - Cross-compiler for aarch64 (TX2 and Nano)
- - Published as wpilib/aarch-cross-ubuntu:target version-host ubuntu version
-   (e.g. bionic-18.04)
- - Minimal variant published as raspbian-cross-ubuntu-aarch64
+ - Published as wpilib/aarch-cross-debian:host debian codename
+   (e.g. trixie)
+ - Minimal variant published as wpilib/aarch64-cross-debian-minimal
 
-roborio-cross-ubuntu-pyXXX
-raspbian-cross-ubuntu-pyXXX
+systemcore-cross-debian-pyXXX
 - Based on the minimal cross compiler image
 - Contains crossenv at /build/venv for cross-compiling python wheels
-- Published as wpilib/{type}-cross-ubuntu:{version}-{ubuntu}-py{pyversion}
+- Published as wpilib/systemcore-cross-debian:{debian}-py{pyversion}
\ No newline at end of file
diff --git a/aarch64-cross-ubuntu/Dockerfile.bookworm-2025 b/aarch64-cross-debian/Dockerfile.trixie
similarity index 62%
rename from aarch64-cross-ubuntu/Dockerfile.bookworm-2025
rename to aarch64-cross-debian/Dockerfile.trixie
index acc8963..0349b42 100644
--- a/aarch64-cross-ubuntu/Dockerfile.bookworm-2025
+++ b/aarch64-cross-debian/Dockerfile.trixie
@@ -1,8 +1,8 @@
-ARG UBUNTU=22.04
+ARG DEBIAN=trixie
 ARG TYPE=base
-FROM wpilib/ubuntu-${TYPE}:${UBUNTU}
+FROM wpilib/debian-${TYPE}:${DEBIAN}
 
 # Install toolchain
-RUN curl -SL https://github.com/wpilibsuite/opensdk/releases/download/v2025-1/arm64-bookworm-2025-x86_64-linux-gnu-Toolchain-12.2.0.tgz | sh -c 'mkdir -p /usr/local && cd /usr/local && tar xzf - --strip-components=2'
+RUN curl -SL https://github.com/wpilibsuite/opensdk/releases/download/v2025-2/arm64-bookworm-2025-x86_64-linux-gnu-Toolchain-12.2.0.tgz | sh -c 'mkdir -p /usr/local && cd /usr/local && tar xzf - --strip-components=2'
 
 WORKDIR /
diff --git a/cross-ubuntu-py/0001-Use-specified-host_cpu-when-cross-compiling-for-Linu.patch b/cross-debian-py/0001-Use-specified-host_cpu-when-cross-compiling-for-Linu.patch
similarity index 100%
rename from cross-ubuntu-py/0001-Use-specified-host_cpu-when-cross-compiling-for-Linu.patch
rename to cross-debian-py/0001-Use-specified-host_cpu-when-cross-compiling-for-Linu.patch
diff --git a/cross-ubuntu-py/0001-bpo-41916-allow-cross-compiled-python-to-have-pthrea.patch b/cross-debian-py/0001-bpo-41916-allow-cross-compiled-python-to-have-pthrea.patch
similarity index 100%
rename from cross-ubuntu-py/0001-bpo-41916-allow-cross-compiled-python-to-have-pthrea.patch
rename to cross-debian-py/0001-bpo-41916-allow-cross-compiled-python-to-have-pthrea.patch
diff --git a/cross-ubuntu-py/Dockerfile.py313 b/cross-debian-py/Dockerfile.py313
similarity index 92%
rename from cross-ubuntu-py/Dockerfile.py313
rename to cross-debian-py/Dockerfile.py313
index 3371282..b6201a0 100644
--- a/cross-ubuntu-py/Dockerfile.py313
+++ b/cross-debian-py/Dockerfile.py313
@@ -1,9 +1,9 @@
 
-ARG UBUNTU=invalid-ubuntu
+ARG DEBIAN=invalid-debian
 ARG ARCH=invalid-arch
 ARG VERSION=invalid-version
 
-FROM wpilib/${ARCH}-cross-ubuntu-minimal:${VERSION}-${UBUNTU} AS pycompile
+FROM wpilib/${ARCH}-cross-debian-minimal:${DEBIAN} AS pycompile
 
 ARG TARGET_HOST=invalid-target-host
 ARG AC_TARGET_HOST=invalid-ac-target-host
@@ -29,7 +29,7 @@ ENV PREFIX="$INSTALL_DIRECTORY"
 RUN set -xe; \
     apt-get update; \
     apt-get install -y build-essential checkinstall g++ libreadline-dev libncurses-dev libssl-dev \
-        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev lzma-dev libffi-dev zlib1g-dev; \
+        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev libffi-dev zlib1g-dev; \
     # cleanup
     rm -rf /var/lib/apt/lists/*
 
@@ -54,7 +54,7 @@ RUN set -xe; \
 RUN set -xe; \
     # Remove build dependencies -- compilation uses host for some reason
     apt-get remove -y libreadline-dev libncursesw5-dev libssl-dev \
-        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev lzma-dev libffi-dev zlib1g-dev; \
+        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev libffi-dev zlib1g-dev; \
     apt-get autoremove -y;
 
 RUN set -xe; \
@@ -81,7 +81,7 @@ RUN set -xe; \
 # Minimal cross-compilation environment
 #
 
-FROM wpilib/${ARCH}-cross-ubuntu-minimal:${VERSION}-${UBUNTU} AS crossenv
+FROM wpilib/${ARCH}-cross-debian-minimal:${DEBIAN} AS crossenv
 
 RUN set -xe; \
     apt-get update; \
diff --git a/cross-ubuntu-py/Dockerfile.py314 b/cross-debian-py/Dockerfile.py314
similarity index 92%
rename from cross-ubuntu-py/Dockerfile.py314
rename to cross-debian-py/Dockerfile.py314
index 8c91ae4..183ba4d 100644
--- a/cross-ubuntu-py/Dockerfile.py314
+++ b/cross-debian-py/Dockerfile.py314
@@ -1,9 +1,9 @@
 
-ARG UBUNTU=invalid-ubuntu
+ARG DEBIAN=invalid-debian
 ARG ARCH=invalid-arch
 ARG VERSION=invalid-version
 
-FROM wpilib/${ARCH}-cross-ubuntu-minimal:${VERSION}-${UBUNTU} AS pycompile
+FROM wpilib/${ARCH}-cross-debian-minimal:${DEBIAN} AS pycompile
 
 ARG TARGET_HOST=invalid-target-host
 ARG AC_TARGET_HOST=invalid-ac-target-host
@@ -29,7 +29,7 @@ ENV PREFIX="$INSTALL_DIRECTORY"
 RUN set -xe; \
     apt-get update; \
     apt-get install -y build-essential checkinstall g++ libreadline-dev libncurses-dev libssl-dev \
-        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev lzma-dev libffi-dev zlib1g-dev; \
+        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev libffi-dev zlib1g-dev; \
     # cleanup
     rm -rf /var/lib/apt/lists/*
 
@@ -54,7 +54,7 @@ RUN set -xe; \
 RUN set -xe; \
     # Remove build dependencies -- compilation uses host for some reason
     apt-get remove -y libreadline-dev libncursesw5-dev libssl-dev \
-        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev lzma-dev libffi-dev zlib1g-dev; \
+        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev libffi-dev zlib1g-dev; \
     apt-get autoremove -y;
 
 RUN set -xe; \
@@ -81,7 +81,7 @@ RUN set -xe; \
 # Minimal cross-compilation environment
 #
 
-FROM wpilib/${ARCH}-cross-ubuntu-minimal:${VERSION}-${UBUNTU} AS crossenv
+FROM wpilib/${ARCH}-cross-debian-minimal:${DEBIAN} AS crossenv
 
 RUN set -xe; \
     apt-get update; \
diff --git a/cross-ubuntu-py/os-release-systemcore b/cross-debian-py/os-release-systemcore
similarity index 100%
rename from cross-ubuntu-py/os-release-systemcore
rename to cross-debian-py/os-release-systemcore
diff --git a/cross-ubuntu-py/pip-systemcore.conf b/cross-debian-py/pip-systemcore.conf
similarity index 100%
rename from cross-ubuntu-py/pip-systemcore.conf
rename to cross-debian-py/pip-systemcore.conf
diff --git a/cross-debian-py/py.mk b/cross-debian-py/py.mk
new file mode 100644
index 0000000..505e5ad
--- /dev/null
+++ b/cross-debian-py/py.mk
@@ -0,0 +1,70 @@
+
+DEBIAN?=trixie
+YEAR?=2026
+DOCKER_USER?=wpilib
+
+TYPE_SYSTEMCORE=systemcore
+VERSION_SYSTEMCORE=2027
+TARGET_HOST_SYSTEMCORE=aarch64-bookworm-linux-gnu
+AC_TARGET_HOST_SYSTEMCORE=aarch64-bookworm-linux-gnu
+
+
+.PHONY: build/cross-python
+build/cross-python: \
+	build/cross-systemcore-py313 \
+	build/cross-systemcore-py314
+
+
+.PHONY: push/cross-python
+push/cross-python: \
+	push/cross-systemcore-py313 \
+	push/cross-systemcore-py314
+
+# systemcore manylinux tags for crossenv
+SC_ML_VERSIONS := $(shell seq 35 -1 17)
+SC_MANYLINUX_TAGS := $(foreach v,$(SC_ML_VERSIONS),--platform-tag=manylinux_2_$(v)_aarch64)
+
+#
+# Python 3.13
+#
+
+.PHONY: build/cross-systemcore-py313
+build/cross-systemcore-py313:
+	cd cross-debian-py && \
+	docker build . \
+		-t wpilib/$(TYPE_SYSTEMCORE)-cross-debian:$(YEAR)-$(DEBIAN)-py313 \
+		--build-arg DEBIAN=$(DEBIAN) \
+		--build-arg ARCH=$(TYPE_SYSTEMCORE) \
+		--build-arg TARGET_HOST=$(TARGET_HOST_SYSTEMCORE) \
+		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_SYSTEMCORE) \
+		--build-arg VERSION=$(VERSION_SYSTEMCORE) \
+		--build-arg MACHINE_ARG="--machine=systemcore" \
+		--build-arg EXTRA_CROSSENV_ARGS="--platform-tag=linux_systemcore $(SC_MANYLINUX_TAGS) --platform-tag=linux_aarch64" \
+		-f Dockerfile.py313
+
+.PHONY: push/cross-systemcore-py313
+push/cross-systemcore-py313:
+	docker push wpilib/$(TYPE_SYSTEMCORE)-cross-debian:$(YEAR)-$(DEBIAN)-py313
+
+
+#
+# Python 3.14
+#
+
+.PHONY: build/cross-systemcore-py314
+build/cross-systemcore-py314:
+	cd cross-debian-py && \
+	docker build . \
+		-t wpilib/$(TYPE_SYSTEMCORE)-cross-debian:$(YEAR)-$(DEBIAN)-py314 \
+		--build-arg DEBIAN=$(DEBIAN) \
+		--build-arg ARCH=$(TYPE_SYSTEMCORE) \
+		--build-arg TARGET_HOST=$(TARGET_HOST_SYSTEMCORE) \
+		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_SYSTEMCORE) \
+		--build-arg VERSION=$(VERSION_SYSTEMCORE) \
+		--build-arg MACHINE_ARG="--machine=systemcore" \
+		--build-arg EXTRA_CROSSENV_ARGS="--platform-tag=linux_systemcore $(SC_MANYLINUX_TAGS) --platform-tag=linux_aarch64" \
+		-f Dockerfile.py314
+
+.PHONY: push/cross-systemcore-py314
+push/cross-systemcore-py314:
+	docker push wpilib/$(TYPE_SYSTEMCORE)-cross-debian:$(YEAR)-$(DEBIAN)-py314
\ No newline at end of file
diff --git a/cross-ubuntu-py/Dockerfile.py311 b/cross-ubuntu-py/Dockerfile.py311
deleted file mode 100644
index 9afcb4b..0000000
--- a/cross-ubuntu-py/Dockerfile.py311
+++ /dev/null
@@ -1,103 +0,0 @@
-
-ARG UBUNTU=invalid-ubuntu
-ARG ARCH=invalid-arch
-ARG VERSION=invalid-version
-
-FROM wpilib/${ARCH}-cross-ubuntu-minimal:${VERSION}-${UBUNTU} AS pycompile
-
-ARG TARGET_HOST=invalid-target-host
-ARG AC_TARGET_HOST=invalid-ac-target-host
-
-ENV TARGET_HOST=${TARGET_HOST}
-ENV AC_TARGET_HOST=${AC_TARGET_HOST}
-ENV BUILD_HOST="x86_64"
-ENV WORKING_DIRECTORY="/build"
-ENV INSTALL_DIRECTORY="/build/crosspy"
-ENV PYTHON_VERSION="3.11.11"
-ENV PYTHON_FTP_VERSION="3.11.11"
-ENV PYTHON_EXE="python3.11"
-ENV SOURCE_DIRECTORY="Python-$PYTHON_VERSION"
-ENV PYTHON_ARCHIVE="Python-$PYTHON_VERSION.tar.xz"
-ENV PREFIX="$INSTALL_DIRECTORY"
-
-#
-# Python compilation prereqs
-#
-
-RUN set -xe; \
-    apt-get update; \
-    apt-get install -y build-essential checkinstall g++ libreadline-dev libncurses-dev libssl-dev \
-        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev lzma-dev libffi-dev zlib1g-dev; \
-    # cleanup
-    rm -rf /var/lib/apt/lists/*
-
-#
-# Python cross-compilation
-#
-
-COPY 0001-bpo-41916-allow-cross-compiled-python-to-have-pthrea.patch /
-COPY 0001-Use-specified-host_cpu-when-cross-compiling-for-Linu.patch /
-
-RUN set -xe; \
-    mkdir -p "$PREFIX"; \
-    # Download
-    cd $WORKING_DIRECTORY; \
-    wget -c https://www.python.org/ftp/python/$PYTHON_FTP_VERSION/$PYTHON_ARCHIVE; \
-    rm -rf $SOURCE_DIRECTORY; \
-    tar -xf $PYTHON_ARCHIVE; \
-    cd $SOURCE_DIRECTORY; \
-    # patch -pthread CXX issue
-    patch -p1 < /0001-bpo-41916-allow-cross-compiled-python-to-have-pthrea.patch; \
-    # patch arm cpu hardcoding
-    patch -p1 < /0001-Use-specified-host_cpu-when-cross-compiling-for-Linu.patch; \
-    # Build python for host
-    cd $WORKING_DIRECTORY;cd $SOURCE_DIRECTORY; \
-    ./configure --enable-optimizations --with-ensurepip=install; \
-    make -j; \
-    make -j altinstall; \
-    # cross-compile
-    cd $WORKING_DIRECTORY;cd $SOURCE_DIRECTORY; make distclean; \
-    ./configure --host=$TARGET_HOST --build=$BUILD_HOST --prefix=$PREFIX \
-        --with-build-python=$(which $PYTHON_EXE) \
-        --disable-ipv6 \
-        ac_cv_host=$AC_TARGET_HOST \
-        ac_cv_buggy_getaddrinfo=no \
-        ac_cv_file__dev_ptmx=no ac_cv_file__dev_ptc=no \
-        ac_cv_have_long_long_format=yes \
-        ac_cv_pthread_is_default=no ac_cv_pthread=yes ac_cv_cxx_thread=yes; \
-    make -j; \
-    # make install here is fine because we include --prefix in the configure statement
-    make install
-    
-
-#
-# Minimal cross-compilation environment
-#
-
-FROM wpilib/${ARCH}-cross-ubuntu-minimal:${VERSION}-${UBUNTU} AS crossenv
-
-RUN set -xe; \
-    apt-get update; \
-    apt-get install -y \
-        binutils libreadline8 libncursesw6 libssl3 \
-        libsqlite3-0 libgdbm6 libbz2-1.0 liblzma5 libffi8 zlib1g; \
-    rm -rf /var/lib/apt/lists/*
-
-COPY --from=pycompile /usr/local /usr/local
-COPY --from=pycompile /build/crosspy /build/crosspy
-
-ARG ARCH=invalid-arch
-ARG TARGET_HOST=invalid-target-host
-ARG EXTRA_CROSSENV_ARGS=
-
-RUN set -xe; \
-    ldconfig; \
-    python3.11 -m pip install 'crossenv~=1.6.1'; \
-    python3.11 -m crossenv /build/crosspy/bin/python3.11 /build/venv --sysroot=$(${TARGET_HOST}-print-sysroot) --env UNIXCONFDIR=/build/venv/cross/etc ${EXTRA_CROSSENV_ARGS}; \
-    /build/venv/bin/cross-pip install wheel;
-
-COPY pip-${ARCH}.conf /build/venv/cross/pip.conf
-COPY os-release-${ARCH} /build/venv/cross/etc/os-release
-
-ENV RPYBUILD_PARALLEL=1
-
diff --git a/cross-ubuntu-py/Dockerfile.py312 b/cross-ubuntu-py/Dockerfile.py312
deleted file mode 100644
index f6e5d5b..0000000
--- a/cross-ubuntu-py/Dockerfile.py312
+++ /dev/null
@@ -1,109 +0,0 @@
-
-ARG UBUNTU=invalid-ubuntu
-ARG ARCH=invalid-arch
-ARG VERSION=invalid-version
-
-FROM wpilib/${ARCH}-cross-ubuntu-minimal:${VERSION}-${UBUNTU} AS pycompile
-
-ARG TARGET_HOST=invalid-target-host
-ARG AC_TARGET_HOST=invalid-ac-target-host
-
-ENV TARGET_HOST=${TARGET_HOST}
-ENV AC_TARGET_HOST=${AC_TARGET_HOST}
-ENV BUILD_HOST="x86_64"
-ENV WORKING_DIRECTORY="/build"
-ENV INSTALL_DIRECTORY="/build/crosspy"
-ENV PYTHON_VERSION="3.12.8"
-ENV PYTHON_FTP_VERSION="3.12.8"
-ENV PYTHON_EXE="python3.12"
-ENV SOURCE_DIRECTORY="Python-$PYTHON_VERSION"
-ENV PYTHON_ARCHIVE="Python-$PYTHON_VERSION.tar.xz"
-ENV PREFIX="$INSTALL_DIRECTORY"
-
-#
-# Python compilation prereqs
-#
-
-RUN set -xe; \
-    apt-get update; \
-    apt-get install -y build-essential checkinstall g++ libreadline-dev libncurses-dev libssl-dev \
-        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev lzma-dev libffi-dev zlib1g-dev; \
-    # cleanup
-    rm -rf /var/lib/apt/lists/*
-
-#
-# Python cross-compilation
-#
-
-COPY 0001-Use-specified-host_cpu-when-cross-compiling-for-Linu.patch /
-
-RUN set -xe; \
-    mkdir -p "$PREFIX"; \
-    # Download
-    cd $WORKING_DIRECTORY; \
-    wget -c https://www.python.org/ftp/python/$PYTHON_FTP_VERSION/$PYTHON_ARCHIVE; \
-    rm -rf $SOURCE_DIRECTORY; \
-    tar -xf $PYTHON_ARCHIVE; \
-    cd $SOURCE_DIRECTORY; \
-    # patch arm cpu hardcoding
-    patch -p1 < /0001-Use-specified-host_cpu-when-cross-compiling-for-Linu.patch; \
-    # Build python for host
-    cd $WORKING_DIRECTORY;cd $SOURCE_DIRECTORY; \
-    ./configure --enable-optimizations --with-ensurepip=install; \
-    make -j; \
-    make -j altinstall
-
-RUN set -xe; \
-    # Remove build dependencies -- compilation uses host for some reason
-    apt-get remove -y libreadline-dev libncursesw5-dev libssl-dev \
-        libsqlite3-dev tk-dev libgdbm-dev libc6-dev libbz2-dev liblzma-dev lzma-dev libffi-dev zlib1g-dev; \
-    apt-get autoremove -y;
-
-RUN set -xe; \
-    # cross-compile
-    cd $WORKING_DIRECTORY;cd $SOURCE_DIRECTORY; make distclean; \
-    ./configure --host=$TARGET_HOST --build=$BUILD_HOST --prefix=$PREFIX \
-        --with-build-python=$(which $PYTHON_EXE) \
-        --disable-ipv6 \
-        ac_cv_host=$AC_TARGET_HOST \
-        ac_cv_buggy_getaddrinfo=no \
-        ac_cv_file__dev_ptmx=no ac_cv_file__dev_ptc=no \
-        ac_cv_have_long_long_format=yes \
-        ac_cv_pthread_is_default=no ac_cv_pthread=yes ac_cv_cxx_thread=yes; \
-    make -j; \
-    # make install here is fine because we include --prefix in the configure statement
-    make install
-    
-
-#
-# Minimal cross-compilation environment
-#
-
-FROM wpilib/${ARCH}-cross-ubuntu-minimal:${VERSION}-${UBUNTU} AS crossenv
-
-RUN set -xe; \
-    apt-get update; \
-    apt-get install -y \
-        binutils libreadline8 libncursesw6 libssl3 \
-        libsqlite3-0 libgdbm6 libbz2-1.0 liblzma5 libffi8 zlib1g; \
-    rm -rf /var/lib/apt/lists/*
-
-COPY --from=pycompile /usr/local /usr/local
-COPY --from=pycompile /build/crosspy /build/crosspy
-
-ARG ARCH=invalid-arch
-ARG TARGET_HOST=invalid-target-host
-ARG MACHINE_ARG=
-ARG EXTRA_CROSSENV_ARGS=
-
-RUN set -xe; \
-    ldconfig; \
-    python3.12 -m pip install 'crossenv~=1.6.1'; \
-    python3.12 -m crossenv /build/crosspy/bin/python3.12 /build/venv ${MACHINE_ARG} --sysroot=$(${TARGET_HOST}-gcc -print-sysroot) --env UNIXCONFDIR=/build/venv/cross/etc ${EXTRA_CROSSENV_ARGS}; \
-    /build/venv/bin/cross-pip install wheel;
-
-COPY pip-${ARCH}.conf /build/venv/cross/pip.conf
-COPY os-release-${ARCH} /build/venv/cross/etc/os-release
-
-ENV RPYBUILD_PARALLEL=1
-
diff --git a/cross-ubuntu-py/Dockerfile.raspbian-2027 b/cross-ubuntu-py/Dockerfile.raspbian-2027
deleted file mode 100644
index 075eacb..0000000
--- a/cross-ubuntu-py/Dockerfile.raspbian-2027
+++ /dev/null
@@ -1,5 +0,0 @@
-ARG IMAGE=invalid-image
-
-FROM ${IMAGE}
-
-COPY pip-raspbian-2027.conf /build/venv/cross/pip.conf
diff --git a/cross-ubuntu-py/os-release-raspbian b/cross-ubuntu-py/os-release-raspbian
deleted file mode 100644
index 989a01d..0000000
--- a/cross-ubuntu-py/os-release-raspbian
+++ /dev/null
@@ -1,10 +0,0 @@
-PRETTY_NAME="Raspbian GNU/Linux 12 (bookworm)"
-NAME="Raspbian GNU/Linux"
-VERSION_ID="12"
-VERSION="12 (bookworm)"
-VERSION_CODENAME=bookworm
-ID=raspbian
-ID_LIKE=debian
-HOME_URL="http://www.raspbian.org/"
-SUPPORT_URL="http://www.raspbian.org/RaspbianForums"
-BUG_REPORT_URL="http://www.raspbian.org/RaspbianBugs"
diff --git a/cross-ubuntu-py/os-release-roborio b/cross-ubuntu-py/os-release-roborio
deleted file mode 100644
index fcae265..0000000
--- a/cross-ubuntu-py/os-release-roborio
+++ /dev/null
@@ -1,5 +0,0 @@
-ID="nilrt-academic"
-NAME="NI Linux Real-Time - Academic"
-VERSION="8.15"
-VERSION_ID="8.15"
-PRETTY_NAME="NI Linux Real-Time - Academic 8.15"
\ No newline at end of file
diff --git a/cross-ubuntu-py/pip-raspbian-2027.conf b/cross-ubuntu-py/pip-raspbian-2027.conf
deleted file mode 100644
index ac5bf1d..0000000
--- a/cross-ubuntu-py/pip-raspbian-2027.conf
+++ /dev/null
@@ -1,5 +0,0 @@
-
-[global]
-extra-index-url = 
-    https://wpilib.jfrog.io/artifactory/api/pypi/wpilib-python-release-2027/simple
-    https://www.piwheels.org/simple
\ No newline at end of file
diff --git a/cross-ubuntu-py/pip-raspbian.conf b/cross-ubuntu-py/pip-raspbian.conf
deleted file mode 100644
index db938f5..0000000
--- a/cross-ubuntu-py/pip-raspbian.conf
+++ /dev/null
@@ -1,5 +0,0 @@
-
-[global]
-extra-index-url = 
-    https://wpilib.jfrog.io/artifactory/api/pypi/wpilib-python-release-2026/simple
-    https://www.piwheels.org/simple
\ No newline at end of file
diff --git a/cross-ubuntu-py/pip-roborio.conf b/cross-ubuntu-py/pip-roborio.conf
deleted file mode 100644
index 2e5cc25..0000000
--- a/cross-ubuntu-py/pip-roborio.conf
+++ /dev/null
@@ -1,3 +0,0 @@
-
-[global]
-extra-index-url = https://wpilib.jfrog.io/artifactory/api/pypi/wpilib-python-release-2026/simple
diff --git a/cross-ubuntu-py/py.mk b/cross-ubuntu-py/py.mk
deleted file mode 100644
index cc43788..0000000
--- a/cross-ubuntu-py/py.mk
+++ /dev/null
@@ -1,244 +0,0 @@
-
-UBUNTU?=22.04
-YEAR?=2026
-DOCKER_USER?=wpilib
-
-TYPE_RASPBIAN=raspbian
-VERSION_RASPBIAN=bookworm
-TARGET_HOST_RASPBIAN=armv6-bookworm-linux-gnueabihf
-AC_TARGET_HOST_RASPBIAN=armv7l-bookworm-linux-gnueabihf
-
-TYPE_ROBORIO=roborio
-VERSION_ROBORIO=2025
-TARGET_HOST_ROBORIO=arm-frc2025-linux-gnueabi
-AC_TARGET_HOST_ROBORIO=armv7l-frc2025-linux-gnueabi
-
-TYPE_SYSTEMCORE=systemcore
-VERSION_SYSTEMCORE=2027
-TARGET_HOST_SYSTEMCORE=aarch64-bookworm-linux-gnu
-AC_TARGET_HOST_SYSTEMCORE=aarch64-bookworm-linux-gnu
-
-
-.PHONY: build/cross-python
-build/cross-python: \
-	build/cross-raspbian-py311 \
-	build/cross-raspbian-py312 \
-	build/cross-roborio-py313 build/cross-systemcore-py313 build/cross-raspbian-py313 \
-	build/cross-roborio-py314 build/cross-systemcore-py314 build/cross-raspbian-py314
-
-
-.PHONY: push/cross-python
-push/cross-python: \
-	push/cross-raspbian-py311 \
-	push/cross-raspbian-py312 \
-	push/cross-roborio-py313 push/cross-systemcore-py313 push/cross-raspbian-py313 \
-	push/cross-roborio-py313 push/cross-systemcore-py314 push/cross-raspbian-py314
-
-
-# raspbian manylinux tags for crossenv
-RPI_ML_VERSIONS := $(shell seq 36 -1 17)
-RPI_MANYLINUX_TAGS := $(foreach v,$(RPI_ML_VERSIONS),--platform-tag=manylinux_2_$(v)_armv7l)
-
-# systemcore manylinux tags for crossenv
-SC_ML_VERSIONS := $(shell seq 35 -1 17)
-SC_MANYLINUX_TAGS := $(foreach v,$(SC_ML_VERSIONS),--platform-tag=manylinux_2_$(v)_aarch64)
-
-
-#
-# Python 3.11
-#
-
-.PHONY: build/cross-raspbian-py311
-build/cross-raspbian-py311:
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py311 \
-		--build-arg UBUNTU=$(UBUNTU) \
-		--build-arg ARCH=$(TYPE_RASPBIAN) \
-		--build-arg TARGET_HOST=$(TARGET_HOST_RASPBIAN) \
-		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_RASPBIAN) \
-		--build-arg VERSION=$(VERSION_RASPBIAN) \
-		--build-arg EXTRA_CROSSENV_ARGS="$(RPI_MANYLINUX_TAGS) --platform-tag=linux_armv7l" \
-		-f Dockerfile.py311
-
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:2027-$(VERSION_RASPBIAN)-$(UBUNTU)-py311 \
-		--build-arg IMAGE=wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py311 \
-		-f Dockerfile.raspbian-2027
-
-.PHONY: push/cross-raspbian-py311
-push/cross-raspbian-py311:
-	docker push wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py311
-
-	docker push wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:2027-$(VERSION_RASPBIAN)-$(UBUNTU)-py311
-
-
-#
-# Python 3.12
-#
-
-.PHONY: build/cross-raspbian-py312
-build/cross-raspbian-py312:
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py312 \
-		--build-arg UBUNTU=$(UBUNTU) \
-		--build-arg ARCH=$(TYPE_RASPBIAN) \
-		--build-arg TARGET_HOST=$(TARGET_HOST_RASPBIAN) \
-		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_RASPBIAN) \
-		--build-arg VERSION=$(VERSION_RASPBIAN) \
-		--build-arg EXTRA_CROSSENV_ARGS="$(RPI_MANYLINUX_TAGS) --platform-tag=linux_armv7l" \
-		-f Dockerfile.py312
-
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:2027-$(VERSION_RASPBIAN)-$(UBUNTU)-py312 \
-		--build-arg IMAGE=wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py312 \
-		-f Dockerfile.raspbian-2027
-
-.PHONY: push/cross-raspbian-py312
-push/cross-raspbian-py312:
-	docker push wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py312
-
-	docker push wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:2027-$(VERSION_RASPBIAN)-$(UBUNTU)-py312
-
-
-#
-# Python 3.13
-#
-
-.PHONY: build/cross-raspbian-py313
-build/cross-raspbian-py313:
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py313 \
-		--build-arg UBUNTU=$(UBUNTU) \
-		--build-arg ARCH=$(TYPE_RASPBIAN) \
-		--build-arg TARGET_HOST=$(TARGET_HOST_RASPBIAN) \
-		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_RASPBIAN) \
-		--build-arg VERSION=$(VERSION_RASPBIAN) \
-		--build-arg EXTRA_CROSS_CONFIGURE_ARGS="ac_cv_libatomic_needed=yes" \
-		--build-arg EXTRA_CROSSENV_ARGS="$(RPI_MANYLINUX_TAGS) --platform-tag=linux_armv7l" \
-		-f Dockerfile.py313
-
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:2027-$(VERSION_RASPBIAN)-$(UBUNTU)-py313 \
-		--build-arg IMAGE=wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py313 \
-		-f Dockerfile.raspbian-2027
-
-.PHONY: push/cross-raspbian-py313
-push/cross-raspbian-py313:
-	docker push wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py313
-
-	docker push wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:2027-$(VERSION_RASPBIAN)-$(UBUNTU)-py313
-
-
-.PHONY: build/cross-roborio-py313
-build/cross-roborio-py313:
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_ROBORIO)-cross-ubuntu:$(YEAR)-$(UBUNTU)-py313 \
-		--build-arg UBUNTU=$(UBUNTU) \
-		--build-arg ARCH=$(TYPE_ROBORIO) \
-		--build-arg TARGET_HOST=$(TARGET_HOST_ROBORIO) \
-		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_ROBORIO) \
-		--build-arg VERSION=$(VERSION_ROBORIO) \
-		--build-arg MACHINE_ARG="--machine=roborio" \
-		--build-arg EXTRA_CROSSENV_ARGS="--platform-tag=linux_roborio" \
-		-f Dockerfile.py313
-
-.PHONY: push/cross-roborio-py313
-push/cross-roborio-py313:
-	docker push wpilib/$(TYPE_ROBORIO)-cross-ubuntu:$(YEAR)-$(UBUNTU)-py313
-
-
-
-.PHONY: build/cross-systemcore-py313
-build/cross-systemcore-py313:
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_SYSTEMCORE)-cross-ubuntu:$(YEAR)-$(UBUNTU)-py313 \
-		--build-arg UBUNTU=$(UBUNTU) \
-		--build-arg ARCH=$(TYPE_SYSTEMCORE) \
-		--build-arg TARGET_HOST=$(TARGET_HOST_SYSTEMCORE) \
-		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_SYSTEMCORE) \
-		--build-arg VERSION=$(VERSION_SYSTEMCORE) \
-		--build-arg MACHINE_ARG="--machine=systemcore" \
-		--build-arg EXTRA_CROSSENV_ARGS="--platform-tag=linux_systemcore $(SC_MANYLINUX_TAGS) --platform-tag=linux_aarch64" \
-		-f Dockerfile.py313
-
-.PHONY: push/cross-systemcore-py313
-push/cross-systemcore-py313:
-	docker push wpilib/$(TYPE_SYSTEMCORE)-cross-ubuntu:$(YEAR)-$(UBUNTU)-py313
-
-
-#
-# Python 3.14
-#
-
-.PHONY: build/cross-raspbian-py314
-build/cross-raspbian-py314:
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py314 \
-		--build-arg UBUNTU=$(UBUNTU) \
-		--build-arg ARCH=$(TYPE_RASPBIAN) \
-		--build-arg TARGET_HOST=$(TARGET_HOST_RASPBIAN) \
-		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_RASPBIAN) \
-		--build-arg VERSION=$(VERSION_RASPBIAN) \
-		--build-arg EXTRA_CROSS_CONFIGURE_ARGS="ac_cv_libatomic_needed=yes" \
-		--build-arg EXTRA_CROSSENV_ARGS="$(RPI_MANYLINUX_TAGS) --platform-tag=linux_armv7l" \
-		-f Dockerfile.py314
-
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:2027-$(VERSION_RASPBIAN)-$(UBUNTU)-py314 \
-		--build-arg IMAGE=wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py314 \
-		-f Dockerfile.raspbian-2027
-
-.PHONY: push/cross-raspbian-py314
-push/cross-raspbian-py314:
-	docker push wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:$(YEAR)-$(VERSION_RASPBIAN)-$(UBUNTU)-py314
-
-	docker push wpilib/$(TYPE_RASPBIAN)-cross-ubuntu:2027-$(VERSION_RASPBIAN)-$(UBUNTU)-py314
-
-
-.PHONY: build/cross-roborio-py314
-build/cross-roborio-py314:
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_ROBORIO)-cross-ubuntu:$(YEAR)-$(UBUNTU)-py314 \
-		--build-arg UBUNTU=$(UBUNTU) \
-		--build-arg ARCH=$(TYPE_ROBORIO) \
-		--build-arg TARGET_HOST=$(TARGET_HOST_ROBORIO) \
-		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_ROBORIO) \
-		--build-arg VERSION=$(VERSION_ROBORIO) \
-		--build-arg MACHINE_ARG="--machine=roborio" \
-		--build-arg EXTRA_CROSSENV_ARGS="--platform-tag=linux_roborio" \
-		-f Dockerfile.py314
-
-.PHONY: push/cross-roborio-py314
-push/cross-roborio-py314:
-	docker push wpilib/$(TYPE_ROBORIO)-cross-ubuntu:$(YEAR)-$(UBUNTU)-py314
-
-
-
-.PHONY: build/cross-systemcore-py314
-build/cross-systemcore-py314:
-	cd cross-ubuntu-py && \
-	docker build . \
-		-t wpilib/$(TYPE_SYSTEMCORE)-cross-ubuntu:$(YEAR)-$(UBUNTU)-py314 \
-		--build-arg UBUNTU=$(UBUNTU) \
-		--build-arg ARCH=$(TYPE_SYSTEMCORE) \
-		--build-arg TARGET_HOST=$(TARGET_HOST_SYSTEMCORE) \
-		--build-arg AC_TARGET_HOST=$(AC_TARGET_HOST_SYSTEMCORE) \
-		--build-arg VERSION=$(VERSION_SYSTEMCORE) \
-		--build-arg MACHINE_ARG="--machine=systemcore" \
-		--build-arg EXTRA_CROSSENV_ARGS="--platform-tag=linux_systemcore $(SC_MANYLINUX_TAGS) --platform-tag=linux_aarch64" \
-		-f Dockerfile.py314
-
-.PHONY: push/cross-systemcore-py314
-push/cross-systemcore-py314:
-	docker push wpilib/$(TYPE_SYSTEMCORE)-cross-ubuntu:$(YEAR)-$(UBUNTU)-py314
\ No newline at end of file
diff --git a/debian-base/Dockerfile.bookworm b/debian-base/Dockerfile.arm64.trixie
similarity index 54%
rename from debian-base/Dockerfile.bookworm
rename to debian-base/Dockerfile.arm64.trixie
index d7181df..7698f56 100644
--- a/debian-base/Dockerfile.bookworm
+++ b/debian-base/Dockerfile.arm64.trixie
@@ -1,13 +1,11 @@
-FROM debian:bookworm
+FROM debian:trixie
 
 RUN apt-get update && apt-get install -y apt-transport-https \
     ca-certificates \
     gnupg \
-    software-properties-common \
     tzdata \
     build-essential \
     ca-certificates \
-    clang-format-14 \
     cmake \
     curl \
     fakeroot \
@@ -16,7 +14,6 @@ RUN apt-get update && apt-get install -y apt-transport-https \
     gdb \
     gfortran \
     git \
-    java-common \
     libc6-dev \
     libgl1-mesa-dev \
     libglu1-mesa-dev \
@@ -31,20 +28,16 @@ RUN apt-get update && apt-get install -y apt-transport-https \
     libxrandr-dev \
     make \
     mesa-common-dev \
+    openjdk-25-jdk \
     python3-dev \
     python3-pip \
     python3-setuptools \
     sudo \
     unzip \
     wget \
-    zip
+    zip \
+  && rm -rf /var/lib/apt/lists/*
 
-RUN curl https://packages.adoptium.net/artifactory/api/gpg/key/public | gpg --dearmor | tee /etc/apt/trusted.gpg.d/adoptium.gpg > /dev/null
-
-RUN echo "deb https://packages.adoptium.net/artifactory/deb $(awk -F= '/^VERSION_CODENAME/{print$2}' /etc/os-release) main" | tee /etc/apt/sources.list.d/adoptium.list
-
-RUN apt update && apt install -y temurin-21-jdk && rm -rf /var/lib/apt/lists/*
-
-ENV JAVA_HOME=/usr/lib/jvm/temurin-21-jdk-arm64
+ENV JAVA_HOME=/usr/lib/jvm/java-25-openjdk-arm64
 
 WORKDIR /
diff --git a/ubuntu-base/Dockerfile.24.04 b/debian-base/Dockerfile.x64.trixie
similarity index 52%
rename from ubuntu-base/Dockerfile.24.04
rename to debian-base/Dockerfile.x64.trixie
index 45f5fb5..20fd662 100644
--- a/ubuntu-base/Dockerfile.24.04
+++ b/debian-base/Dockerfile.x64.trixie
@@ -1,17 +1,11 @@
-FROM ubuntu:24.04
+FROM debian:trixie
 
 RUN apt-get update && apt-get install -y apt-transport-https \
     ca-certificates \
     gnupg \
-    software-properties-common \
-    wget && \
-    wget -O - https://apt.kitware.com/keys/kitware-archive-latest.asc 2>/dev/null | gpg --dearmor - | tee /usr/share/keyrings/kitware-archive-keyring.gpg >/dev/null && \
-    echo 'deb [signed-by=/usr/share/keyrings/kitware-archive-keyring.gpg] https://apt.kitware.com/ubuntu/ noble main' > /etc/apt/sources.list.d/kitware.list && \
-    add-apt-repository ppa:git-core/ppa && \
-    apt-get update && apt-get install -y tzdata && apt-get install -y \
+    tzdata \
     build-essential \
     ca-certificates \
-    clang-format-14 \
     cmake \
     curl \
     fakeroot \
@@ -20,7 +14,6 @@ RUN apt-get update && apt-get install -y apt-transport-https \
     gdb \
     gfortran \
     git \
-    java-common \
     libc6-dev \
     libgl1-mesa-dev \
     libglu1-mesa-dev \
@@ -35,7 +28,7 @@ RUN apt-get update && apt-get install -y apt-transport-https \
     libxrandr-dev \
     make \
     mesa-common-dev \
-    openjdk-17-jdk \
+    openjdk-25-jdk \
     python3-dev \
     python3-pip \
     python3-setuptools \
@@ -45,6 +38,6 @@ RUN apt-get update && apt-get install -y apt-transport-https \
     zip \
   && rm -rf /var/lib/apt/lists/*
 
-ENV JAVA_HOME=/usr/lib/jvm/java-17-openjdk-amd64
+ENV JAVA_HOME=/usr/lib/jvm/java-25-openjdk-amd64
 
 WORKDIR /
diff --git a/ubuntu-minimal-base/Dockerfile.22.04 b/debian-minimal-base/Dockerfile.trixie
similarity index 86%
rename from ubuntu-minimal-base/Dockerfile.22.04
rename to debian-minimal-base/Dockerfile.trixie
index 80b478f..8d2024f 100644
--- a/ubuntu-minimal-base/Dockerfile.22.04
+++ b/debian-minimal-base/Dockerfile.trixie
@@ -1,5 +1,4 @@
-ARG UBUNTU=22.04
-FROM ubuntu:${UBUNTU}
+FROM debian:trixie
 
 RUN set -xe; \
     apt-get update; \
diff --git a/raspbian-cross-ubuntu/Dockerfile.bookworm-2025 b/raspbian-cross-ubuntu/Dockerfile.bookworm-2025
deleted file mode 100644
index f560415..0000000
--- a/raspbian-cross-ubuntu/Dockerfile.bookworm-2025
+++ /dev/null
@@ -1,9 +0,0 @@
-ARG UBUNTU=22.04
-ARG TYPE=base
-FROM wpilib/ubuntu-${TYPE}:${UBUNTU}
-
-
-# Install toolchain
-RUN curl -SL https://github.com/wpilibsuite/opensdk/releases/download/v2025-1/armhf-raspi-bookworm-2025-x86_64-linux-gnu-Toolchain-12.2.0.tgz | sh -c 'mkdir -p /usr/local && cd /usr/local && tar xzf - --strip-components=2'
-
-WORKDIR /
diff --git a/raspbian-cross-ubuntu/Dockerfile.bookworm-2027 b/raspbian-cross-ubuntu/Dockerfile.bookworm-2027
deleted file mode 100644
index b13594c..0000000
--- a/raspbian-cross-ubuntu/Dockerfile.bookworm-2027
+++ /dev/null
@@ -1,13 +0,0 @@
-ARG UBUNTU=24.04
-ARG TYPE=base
-FROM wpilib/ubuntu-${TYPE}:${UBUNTU}
-
-
-# Install toolchain
-RUN curl -SL https://github.com/wpilibsuite/opensdk/releases/download/v2025-2/armhf-raspi-bookworm-2025-x86_64-linux-gnu-Toolchain-12.2.0.tgz | sh -c 'mkdir -p /usr/local && cd /usr/local && tar xzf - --strip-components=2'
-
-RUN apt update && apt install -y openjdk-25-jdk && rm -rf /var/lib/apt/lists/*
-
-ENV JAVA_HOME=/usr/lib/jvm/java-25-openjdk-amd64
-
-WORKDIR /
diff --git a/roborio-cross-ubuntu/Dockerfile.2025 b/roborio-cross-ubuntu/Dockerfile.2025
deleted file mode 100644
index 9bedc94..0000000
--- a/roborio-cross-ubuntu/Dockerfile.2025
+++ /dev/null
@@ -1,8 +0,0 @@
-ARG UBUNTU=22.04
-ARG TYPE=base
-FROM wpilib/ubuntu-${TYPE}:${UBUNTU}
-
-# Install toolchain
-RUN curl -SL https://github.com/wpilibsuite/opensdk/releases/download/v2025-1/cortexa9_vfpv3-roborio-academic-2025-x86_64-linux-gnu-Toolchain-12.1.0.tgz | sh -c 'mkdir -p /usr/local && cd /usr/local && tar xzf - --strip-components=2'
-
-WORKDIR /
diff --git a/aarch64-cross-ubuntu/Dockerfile.bookworm-2027 b/systemcore-cross-debian/Dockerfile.trixie
similarity index 59%
rename from aarch64-cross-ubuntu/Dockerfile.bookworm-2027
rename to systemcore-cross-debian/Dockerfile.trixie
index be51352..b9afd37 100644
--- a/aarch64-cross-ubuntu/Dockerfile.bookworm-2027
+++ b/systemcore-cross-debian/Dockerfile.trixie
@@ -1,12 +1,10 @@
-ARG UBUNTU=24.04
+ARG VERSION=trixie
 ARG TYPE=base
-FROM wpilib/ubuntu-${TYPE}:${UBUNTU}
+FROM wpilib/debian-${TYPE}:${VERSION}
 
 # Install toolchain
 RUN curl -SL https://github.com/wpilibsuite/opensdk/releases/download/v2025-2/arm64-bookworm-2025-x86_64-linux-gnu-Toolchain-12.2.0.tgz | sh -c 'mkdir -p /usr/local && cd /usr/local && tar xzf - --strip-components=2'
 
-RUN apt update && apt install -y openjdk-25-jdk && rm -rf /var/lib/apt/lists/*
-
-ENV JAVA_HOME=/usr/lib/jvm/java-25-openjdk-amd64
+RUN apt update && apt install -y avahi-daemon && rm -rf /var/lib/apt/lists/*
 
 WORKDIR /
diff --git a/systemcore-cross-ubuntu/Dockerfile.2027 b/systemcore-cross-ubuntu/Dockerfile.2027
deleted file mode 100644
index 4848585..0000000
--- a/systemcore-cross-ubuntu/Dockerfile.2027
+++ /dev/null
@@ -1,12 +0,0 @@
-ARG UBUNTU=22.04
-ARG TYPE=base
-FROM wpilib/ubuntu-${TYPE}:${UBUNTU}
-
-# Install toolchain
-RUN curl -SL https://github.com/wpilibsuite/opensdk/releases/download/v2025-2/arm64-bookworm-2025-x86_64-linux-gnu-Toolchain-12.2.0.tgz | sh -c 'mkdir -p /usr/local && cd /usr/local && tar xzf - --strip-components=2'
-
-RUN apt update && apt install -y openjdk-25-jdk avahi-daemon && rm -rf /var/lib/apt/lists/*
-
-ENV JAVA_HOME=/usr/lib/jvm/java-25-openjdk-amd64
-
-WORKDIR /
diff --git a/ubuntu-base/Dockerfile.22.04 b/ubuntu-base/Dockerfile.22.04
deleted file mode 100644
index 7a0859b..0000000
--- a/ubuntu-base/Dockerfile.22.04
+++ /dev/null
@@ -1,51 +0,0 @@
-FROM ubuntu:22.04
-
-RUN apt-get update && apt-get install -y apt-transport-https \
-    ca-certificates \
-    gnupg \
-    software-properties-common \
-    wget && \
-    wget -O - https://apt.kitware.com/keys/kitware-archive-latest.asc 2>/dev/null | gpg --dearmor - | tee /usr/share/keyrings/kitware-archive-keyring.gpg >/dev/null && \
-    echo 'deb [signed-by=/usr/share/keyrings/kitware-archive-keyring.gpg] https://apt.kitware.com/ubuntu/ jammy main' > /etc/apt/sources.list.d/kitware.list && \
-    add-apt-repository ppa:git-core/ppa && \
-    apt-get update && apt-get install -y tzdata && apt-get install -y \
-    build-essential \
-    ca-certificates \
-    clang-format-14 \
-    cmake \
-    curl \
-    fakeroot \
-    g++ --no-install-recommends \
-    gcc \
-    gdb \
-    gfortran \
-    git \
-    java-common \
-    libc6-dev \
-    libgl1-mesa-dev \
-    libglu1-mesa-dev \
-    libisl-dev \
-    libopencv-dev \
-    libopencv4.5-java \
-    libvulkan-dev \
-    libx11-dev \
-    libxcursor-dev \
-    libxi-dev \
-    libxinerama-dev \
-    libxrandr-dev \
-    make \
-    mesa-common-dev \
-    openjdk-17-jdk \
-    python-all-dev \
-    python3-dev \
-    python3-pip \
-    python3-setuptools \
-    sudo \
-    unzip \
-    wget \
-    zip \
-  && rm -rf /var/lib/apt/lists/*
-
-ENV JAVA_HOME=/usr/lib/jvm/java-17-openjdk-amd64
-
-WORKDIR /
diff --git a/ubuntu-minimal-base/Dockerfile.24.04 b/ubuntu-minimal-base/Dockerfile.24.04
deleted file mode 100644
index 7bd66d3..0000000
--- a/ubuntu-minimal-base/Dockerfile.24.04
+++ /dev/null
@@ -1,17 +0,0 @@
-ARG UBUNTU=24.04
-FROM ubuntu:${UBUNTU}
-
-RUN set -xe; \
-    apt-get update; \
-    apt-get install -y tzdata; \
-    apt-get install -y \
-        ca-certificates \
-        curl \
-        git \
-        make \
-        unzip \
-        wget \
-        zip; \
-    rm -rf /var/lib/apt/lists/*
-
-WORKDIR /