diff --git a/.github/promote-images.yml b/.github/promote-images.yml
index feea562d6..614de0470 100644
--- a/.github/promote-images.yml
+++ b/.github/promote-images.yml
@@ -19,7 +19,6 @@
     workspace-node-22: "TIMESTAMP_TAG"
     workspace-node-23: "TIMESTAMP_TAG"
     workspace-python: "TIMESTAMP_TAG"
-    workspace-python-3.9: "TIMESTAMP_TAG"
     workspace-python-3.10: "TIMESTAMP_TAG"
     workspace-python-3.11: "TIMESTAMP_TAG"
     workspace-python-3.12: "TIMESTAMP_TAG"
diff --git a/.github/sync-containers.yml b/.github/sync-containers.yml
index 7ed806bbc..84fa3b6d0 100644
--- a/.github/sync-containers.yml
+++ b/.github/sync-containers.yml
@@ -16,7 +16,6 @@ sync:
     - node-22
     - node-23
     - python
-    - python-3.9
     - python-3.10
     - python-3.11
     - python-3.12
diff --git a/.gitpod/automations.yaml b/.gitpod/automations.yaml
index 3404c27b5..72b31e110 100644
--- a/.gitpod/automations.yaml
+++ b/.gitpod/automations.yaml
@@ -4,6 +4,7 @@ tasks:
     description: 'Starts the buildkit daemon for Docker image building'
     triggeredBy:
       - postDevcontainerStart
+      - postEnvironmentStart
     command: |
       sudo /usr/bin/buildkitd --debug --config ./buildkitd.toml --group gitpod
   start-docker-registry:
@@ -11,6 +12,7 @@ tasks:
     description: 'Starts a local Docker registry on port 5000 for dazzle builds'
     triggeredBy:
       - postDevcontainerStart
+      - postEnvironmentStart
     command: |
       mkdir -p /workspace/registry
       docker run -p 5000:5000 --name registry --rm -v /workspace/registry:/var/lib/registry registry:2
@@ -19,6 +21,7 @@ tasks:
     description: 'Waits for registry to be ready and displays build commands'
     triggeredBy:
       - postDevcontainerStart
+      - postEnvironmentStart
       - manual
     command: |
       # Wait for registry port to be available
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 43c48617c..1dfdb0fb3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,13 @@
 
 A curated, chronologically ordered list of notable changes in [Gitpod's default workspace images](https://hub.docker.com/u/gitpod).
 
+## 2026-01-20
+
+- Remove `gitpod/workspace-python-3.9` (Python 3.9 reached EOL October 2025)
+- Bump `gitpod/workspace-python` and `gitpod/workspace-full` to Python 3.13
+- Bump pyenv to v2.6.20
+- Bump `gitpod/workspace-yugabytedb` images to Python 3.10
+
 ## 2025-09-30
 
 - Introduce `workspace-java-25`
diff --git a/README.md b/README.md
index 9aec9e84b..d2f28fea4 100644
--- a/README.md
+++ b/README.md
@@ -61,7 +61,6 @@ Each contains a set of chunks: a common base and a language / tool. Every image
 - [`gitpod/workspace-node-22`](https://hub.docker.com/r/gitpod/workspace-node-22) ✅
 - [`gitpod/workspace-node-23`](https://hub.docker.com/r/gitpod/workspace-node-23) ✅
 - [`gitpod/workspace-python`](https://hub.docker.com/r/gitpod/workspace-python) ✅
-- [`gitpod/workspace-python-3.9`](https://hub.docker.com/r/gitpod/workspace-python-3.9) ✅
 - [`gitpod/workspace-python-3.10`](https://hub.docker.com/r/gitpod/workspace-python-3.10) ✅
 - [`gitpod/workspace-python-3.11`](https://hub.docker.com/r/gitpod/workspace-python-3.11) ✅
 - [`gitpod/workspace-python-3.12`](https://hub.docker.com/r/gitpod/workspace-python-3.12) ✅
diff --git a/build-chunk.sh b/build-chunk.sh
index 8ecfb9478..6170bc5e3 100755
--- a/build-chunk.sh
+++ b/build-chunk.sh
@@ -1,6 +1,6 @@
 #!/bin/bash
 set -euo pipefail
-trap ctrl_c EXIT
+trap '[[ -f .dazzle.yaml.orig ]] && cp .dazzle.yaml.orig dazzle.yaml' EXIT
 
 # shellcheck source=/dev/null
 source build-common.sh
diff --git a/build-combo.sh b/build-combo.sh
index 95af15c9c..15e440aba 100755
--- a/build-combo.sh
+++ b/build-combo.sh
@@ -1,6 +1,6 @@
 #! /bin/bash
 set -eo pipefail
-trap ctrl_c EXIT
+trap '[[ -f .dazzle.yaml.orig ]] && cp .dazzle.yaml.orig dazzle.yaml' EXIT
 
 # shellcheck source=/dev/null
 source build-common.sh
diff --git a/chunks/lang-python/Dockerfile b/chunks/lang-python/Dockerfile
index 430ef2bf0..28010934c 100644
--- a/chunks/lang-python/Dockerfile
+++ b/chunks/lang-python/Dockerfile
@@ -21,8 +21,8 @@ RUN sudo install-packages \
 	libncursesw5-dev xz-utils tk-dev libxml2-dev libxmlsec1-dev libffi-dev liblzma-dev \
 	# Install PYENV
 	&& git clone https://github.com/pyenv/pyenv.git ~/.pyenv \
-	# v2.6.10
-	&& git -C ~/.pyenv checkout a419b003b4615bef05098865bb97e0fbc428095e \
+	# v2.6.20
+	&& git -C ~/.pyenv checkout 3441980e83bb1c5fdb2f1734ae4dab694d10ef71 \
 	&& pyenv install ${PYTHON_VERSION} \
 	&& pyenv global ${PYTHON_VERSION} \
 	&& for exec in global; do printf '%s\n' 'source "$HOME/.gp_pyenv.d/userbase.bash"' >> "$PYENV_ROOT/libexec/pyenv-$exec"; done \
diff --git a/chunks/lang-python/chunk.yaml b/chunks/lang-python/chunk.yaml
index 3b3ef09b6..72294add3 100644
--- a/chunks/lang-python/chunk.yaml
+++ b/chunks/lang-python/chunk.yaml
@@ -1,7 +1,7 @@
 variants:
   - name: "3.13"
     args:
-      PYTHON_VERSION: 3.13.8
+      PYTHON_VERSION: 3.13.11
   - name: "3.12"
     args:
       PYTHON_VERSION: 3.12.12
@@ -11,6 +11,3 @@ variants:
   - name: "3.10"
     args:
       PYTHON_VERSION: 3.10.19
-  - name: "3.9"
-    args:
-      PYTHON_VERSION: 3.9.24
diff --git a/chunks/tool-yugabytedb/Dockerfile b/chunks/tool-yugabytedb/Dockerfile
index abde512b5..266e04368 100644
--- a/chunks/tool-yugabytedb/Dockerfile
+++ b/chunks/tool-yugabytedb/Dockerfile
@@ -24,14 +24,13 @@ RUN curl -sSLo ./yugabyte.tar.gz https://downloads.yugabyte.com/releases/${YB_VE
   && rm ./yugabyte.tar.gz
 
 # python is a required dependency of ycqlsh
-# but it doesn't support Python 3.10+ due to https://github.com/yugabyte/cqlsh/issues/11, install 3.9 for now
 # when building yugabyte combos, if our base is full, related python chunk tests fail
 # so, use base as the combo ref, add chunks, but ignore Python chunk and install manually
 ENV PATH="$HOME/.pyenv/bin:$HOME/.pyenv/shims:$PATH"
 ENV PYENV_ROOT="$HOME/.pyenv"
 RUN git clone https://github.com/pyenv/pyenv.git ~/.pyenv \
-  # v2.6.10
-  && git -C ~/.pyenv checkout a419b003b4615bef05098865bb97e0fbc428095e \
+  # v2.6.20
+  && git -C ~/.pyenv checkout 3441980e83bb1c5fdb2f1734ae4dab694d10ef71 \
   && pyenv install ${PYTHON_VERSION} \
   && pyenv global ${PYTHON_VERSION}
 
diff --git a/chunks/tool-yugabytedb/chunk.yaml b/chunks/tool-yugabytedb/chunk.yaml
index daf1ab7e3..726a0d5dc 100644
--- a/chunks/tool-yugabytedb/chunk.yaml
+++ b/chunks/tool-yugabytedb/chunk.yaml
@@ -3,14 +3,14 @@ variants:
     args:
       YB_VERSION: 2.18.4.2
       YB_BUILD: 2
-      PYTHON_VERSION: 3.9
+      PYTHON_VERSION: 3.10
   - name: "2.19"
     args:
       YB_VERSION: 2.19.3.0
       YB_BUILD: 140
-      PYTHON_VERSION: 3.9
+      PYTHON_VERSION: 3.10
   - name: "2.20"
     args:
       YB_VERSION: 2.20.1.3
       YB_BUILD: 3
-      PYTHON_VERSION: 3.9
+      PYTHON_VERSION: 3.10
diff --git a/dazzle.yaml b/dazzle.yaml
index 45b65197c..2c8f65abf 100644
--- a/dazzle.yaml
+++ b/dazzle.yaml
@@ -38,7 +38,7 @@ combiner:
         - lang-go:1.24
         - lang-java:11
         - lang-node:22
-        - lang-python:3.12
+        - lang-python:3.13
         - lang-ruby:3.2
         - lang-rust:1
         - tool-brew
@@ -121,11 +121,6 @@ combiner:
       - base
       chunks:
         - lang-python:3.10
-    - name: python-3.9
-      ref:
-      - base
-      chunks:
-        - lang-python:3.9
     - name: ruby-3.1
       ref:
       - base