diff --git a/CHANGELOG.md b/CHANGELOG.md
index 81a361b..58572a1 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,19 @@
 # Changelog
 
+## Unreleased
+
+## Added
+
+Set `ENV PIP_BREAK_SYSTEM_PACKAGES=1` within the Dockerfile to enable system-wide Python package installations by default, bypassing the externally-managed-environment error (PEP 668). This removes the need to explicitly use --break-system-packages or initialize a virtual environment for global pip installs during the image build process.
+
+## Updated
+
+Kubectl: from v1.33.0 to v1.33.1
+Google Cloud CLI (gcloud): from 519.0.0 to 525.0.0
+AWS CLI: from 2.27.1 to 2.27.32
+Azure CLI: from 2.71.0 to 2.74.0
+Scalr CLI: from 0.17.0 to 0.17.1
+
 ## [0.1.2](https://github.com/Scalr/runner/tree/0.1.2) (2025-05-07)
 
 [Full Changelog](https://github.com/Scalr/runner/compare/0.1.1...0.1.2)
@@ -16,6 +30,4 @@
 
 - SCALRCORE-34486 \> Basic Repository Setup [\#1](https://github.com/Scalr/runner/pull/1) ([artemvang](https://github.com/artemvang))
 
-
-
 \* *This Changelog was automatically generated by [github_changelog_generator](https://github.com/github-changelog-generator/github-changelog-generator)*
diff --git a/Dockerfile b/Dockerfile
index 8288211..78030a5 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -32,6 +32,10 @@ RUN <<EOT
   find /usr -name __pycache__ -type d -exec rm -rf {} +
 EOT
 
+# This effectively makes `pip install --break-system-packages ...` the default, allowing
+# to install packages system-wide without needing to initialize a virtual environment.
+ENV PIP_BREAK_SYSTEM_PACKAGES=1
+
 # Kubectl
 ARG KUBECTL_VERSION
 LABEL kubectl.version=${KUBECTL_VERSION}
diff --git a/README.md b/README.md
index d15c984..2b707fc 100644
--- a/README.md
+++ b/README.md
@@ -1,32 +1,49 @@
-# Runner Image used in Scalr Remote Backend.
+# Runner Image used in Scalr Remote Backend
 
 This is the Git repo of the official runner image.
 
-The image is based on the [`debian:bookworm-slim`](https://hub.docker.com/_/debian),
+The image is based on the [`debian:trixie-slim`](https://hub.docker.com/_/debian),
 and contains the following software:
 
-* Archivators - zip, tar, gzip
-* Encryption - gnupg
-* Git (2.39.5) - core, LFS, ssh/http transports
-* HTTP clients - curl, wget, ca-certificates
-* JSON - jq
-* Python (3.11.2)
-* Cloud clients (see [versions](./versions)):
-  * AWS CLI
-  * Azure CLI
-  * GCloud - Stable, Alpha, and Beta components. Kubectl authenticator
-* Kubectl (latest version)
-* Scalr CLI
+## Included Tools
+
+This environment comes pre-equipped with a comprehensive suite of tools essential for development, operations, and cloud interactions. Here's a breakdown of what's included:
+
+* **Archivators**:
+  * zip - Create and extract ZIP archives
+  * tar - Manipulate tar archives
+  * gzip - Compress and decompress `.gz` files
+* **Encryption**:
+  * gnupg - Secure data encryption and signing
+* **Git (v2.47.2)**:
+  * Core Git functionality
+  * Git LFS (Large File Storage)
+  * SSH and HTTP transport protocols
+* **HTTP Clients**:
+  * curl - Data transfer with URLs
+  * wget - File downloads from the web
+  * ca-certificates - Trusted CA certificates
+* **Programming Languages**
+  * Python ([v3.13.3](https://www.python.org/downloads/release/python-3133/)) - General-purpose programming language (release)
+  * jq - Command-line JSON processor
+* **Cloud Clients**
+  * AWS CLI ([2.27.1](https://github.com/aws/aws-cli/releases/tag/2.27.32)) - Amazon Web Services CLI.
+  * Azure CLI ([2.71.0](https://github.com/Azure/azure-cli/releases/tag/azure-cli-2.74.0)) - Microsoft Azure CLI.
+  * Google Cloud SDK ([525.0.0](https://cloud.google.com/sdk/docs/release-notes#52500_2025-06-03)) - Stable, Alpha, Beta components. Includes kubectl authenticator.
+  * Kubectl ([0.33.1](https://github.com/kubernetes/kubectl/releases/tag/v0.33.1)) - Kubernetes CLI.
+  * Scalr CLI ([0.17.1](https://github.com/Scalr/scalr-cli/releases/tag/v0.17.1)) - The command-line to communicate with the Scalr API.
+
+The versions for Cloud Clients, Kubectl, and Scalr CLI are specifically pinned and detailed in the [versions](./versions) file. All other software included in this environment is sourced directly from the Debian Trixie upstream repositories.
 
 ## Runner Image Building
 
 ```bash
 docker buildx build \
-  --build-arg KUBECTL_VERSION=v1.33.0 \
-  --build-arg GCLOUD_VERSION=519.0.0 \
+  --build-arg KUBECTL_VERSION=v1.33.1 \
+  --build-arg GCLOUD_VERSION=525.0.0 \
   --build-arg AWS_CLI_VERSION=2.27.1 \
   --build-arg AZURE_CLI_VERSION=2.71.0 \
-  --build-arg SCALR_CLI_VERSION=0.17.0 \
+  --build-arg SCALR_CLI_VERSION=0.17.1 \
   --platform linux/amd64 \
   -t runner:latest --load .
-```
\ No newline at end of file
+```
diff --git a/versions b/versions
index 1dba61e..18fd987 100644
--- a/versions
+++ b/versions
@@ -1,5 +1,5 @@
-kubectl=v1.33.0
-gcloud=519.0.0
-aws_cli=2.27.1
-azure_cli=2.71.0
-scalr_cli=0.17.0
+kubectl=v1.33.1
+gcloud=525.0.0
+aws_cli=2.27.32
+azure_cli=2.74.0
+scalr_cli=0.17.1