diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index d8906ad..e736362 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -81,12 +81,15 @@ jobs:
     needs: [test, lint]
     steps:
       - name: Clear Space
-        if: github.event_name == 'pull_request'
+        # Note: Manual cleanup sufficient for CPU images (python:3.12-slim base ~150MB)
+        # Only CUDA images need aggressive cleanup due to their ~10-15GB size
         run: |
           rm -rf /usr/share/dotnet
           rm -rf /opt/ghc
           rm -rf "/usr/local/share/boost"
           rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -132,13 +135,20 @@ jobs:
     runs-on: ubuntu-latest
     needs: [test, lint]
     steps:
-      - name: Clear Space
-        if: github.event_name == 'pull_request'
+      - name: Free Disk Space
+        uses: jlumbroso/free-disk-space@v1.3.1
+        with:
+          tool-cache: true
+          android: true
+          dotnet: true
+          haskell: true
+          large-packages: true
+          swap-storage: true
+
+      - name: Additional cleanup and report
         run: |
-          rm -rf /usr/share/dotnet
-          rm -rf /opt/ghc
-          rm -rf "/usr/local/share/boost"
-          rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -179,13 +189,20 @@ jobs:
     runs-on: ubuntu-latest
     needs: [test, lint]
     steps:
-      - name: Clear Space
-        if: github.event_name == 'pull_request'
+      - name: Free Disk Space
+        uses: jlumbroso/free-disk-space@v1.3.1
+        with:
+          tool-cache: true
+          android: true
+          dotnet: true
+          haskell: true
+          large-packages: true
+          swap-storage: true
+
+      - name: Additional cleanup and report
         run: |
-          rm -rf /usr/share/dotnet
-          rm -rf /opt/ghc
-          rm -rf "/usr/local/share/boost"
-          rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -247,12 +264,20 @@ jobs:
     needs: [test, lint, docker-test, release]
     if: github.ref == 'refs/heads/main' && github.event_name == 'push' && !needs.release.outputs.release_created
     steps:
-      - name: Clear Space
+      - name: Free Disk Space
+        uses: jlumbroso/free-disk-space@v1.3.1
+        with:
+          tool-cache: true
+          android: true
+          dotnet: true
+          haskell: true
+          large-packages: true
+          swap-storage: true
+
+      - name: Additional cleanup and report
         run: |
-          rm -rf /usr/share/dotnet
-          rm -rf /opt/ghc
-          rm -rf "/usr/local/share/boost"
-          rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -306,6 +331,8 @@ jobs:
           rm -rf /opt/ghc
           rm -rf "/usr/local/share/boost"
           rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -353,12 +380,20 @@ jobs:
     needs: [test, lint, docker-test, docker-test-lb, release]
     if: github.ref == 'refs/heads/main' && github.event_name == 'push' && !needs.release.outputs.release_created
     steps:
-      - name: Clear Space
+      - name: Free Disk Space
+        uses: jlumbroso/free-disk-space@v1.3.1
+        with:
+          tool-cache: true
+          android: true
+          dotnet: true
+          haskell: true
+          large-packages: true
+          swap-storage: true
+
+      - name: Additional cleanup and report
         run: |
-          rm -rf /usr/share/dotnet
-          rm -rf /opt/ghc
-          rm -rf "/usr/local/share/boost"
-          rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -406,12 +441,20 @@ jobs:
     needs: [test, lint, docker-test, docker-test-lb-cpu, release]
     if: github.ref == 'refs/heads/main' && github.event_name == 'push' && !needs.release.outputs.release_created
     steps:
-      - name: Clear Space
+      - name: Free Disk Space
+        uses: jlumbroso/free-disk-space@v1.3.1
+        with:
+          tool-cache: true
+          android: true
+          dotnet: true
+          haskell: true
+          large-packages: true
+          swap-storage: true
+
+      - name: Additional cleanup and report
         run: |
-          rm -rf /usr/share/dotnet
-          rm -rf /opt/ghc
-          rm -rf "/usr/local/share/boost"
-          rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -459,12 +502,20 @@ jobs:
     needs: [release]
     if: needs.release.outputs.release_created
     steps:
-      - name: Clear Space
+      - name: Free Disk Space
+        uses: jlumbroso/free-disk-space@v1.3.1
+        with:
+          tool-cache: true
+          android: true
+          dotnet: true
+          haskell: true
+          large-packages: true
+          swap-storage: true
+
+      - name: Additional cleanup and report
         run: |
-          rm -rf /usr/share/dotnet
-          rm -rf /opt/ghc
-          rm -rf "/usr/local/share/boost"
-          rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -528,6 +579,8 @@ jobs:
           rm -rf /opt/ghc
           rm -rf "/usr/local/share/boost"
           rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -585,12 +638,20 @@ jobs:
     needs: [release]
     if: needs.release.outputs.release_created
     steps:
-      - name: Clear Space
+      - name: Free Disk Space
+        uses: jlumbroso/free-disk-space@v1.3.1
+        with:
+          tool-cache: true
+          android: true
+          dotnet: true
+          haskell: true
+          large-packages: true
+          swap-storage: true
+
+      - name: Additional cleanup and report
         run: |
-          rm -rf /usr/share/dotnet
-          rm -rf /opt/ghc
-          rm -rf "/usr/local/share/boost"
-          rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
@@ -648,12 +709,20 @@ jobs:
     needs: [release]
     if: needs.release.outputs.release_created
     steps:
-      - name: Clear Space
+      - name: Free Disk Space
+        uses: jlumbroso/free-disk-space@v1.3.1
+        with:
+          tool-cache: true
+          android: true
+          dotnet: true
+          haskell: true
+          large-packages: true
+          swap-storage: true
+
+      - name: Additional cleanup and report
         run: |
-          rm -rf /usr/share/dotnet
-          rm -rf /opt/ghc
-          rm -rf "/usr/local/share/boost"
-          rm -rf "$AGENT_TOOLSDIRECTORY"
+          docker system prune -af
+          df -h
 
       - name: Checkout repository
         uses: actions/checkout@v4
diff --git a/Dockerfile b/Dockerfile
index cb60949..de8c9b8 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -17,8 +17,11 @@ RUN mkdir -p /root/.cache/apt/archives/partial \
  && echo 'Dir::Cache "/root/.cache/apt";' > /etc/apt/apt.conf.d/01cache
 
 # Install system dependencies and uv
+# Note: build-essential not pre-installed to reduce image size (400MB savings)
+# Automatic detection will install it when needed (no manual action required)
+# Advanced: Users can pre-install via system_dependencies=["build-essential"]
 RUN DEBIAN_FRONTEND=noninteractive apt-get update && apt-get install -y --no-install-recommends \
-    build-essential curl ca-certificates nala git \
+    curl ca-certificates nala git \
  && curl -LsSf https://astral.sh/uv/install.sh | sh \
  && cp ~/.local/bin/uv /usr/local/bin/uv \
  && chmod +x /usr/local/bin/uv \
diff --git a/Dockerfile-cpu b/Dockerfile-cpu
index 65add8c..37e1081 100644
--- a/Dockerfile-cpu
+++ b/Dockerfile-cpu
@@ -12,8 +12,11 @@ RUN mkdir -p /root/.cache/apt/archives/partial \
  && echo 'Dir::Cache "/root/.cache/apt";' > /etc/apt/apt.conf.d/01cache
 
 # Install system dependencies and uv
+# Note: build-essential not pre-installed to reduce image size (400MB savings)
+# Automatic detection will install it when needed (no manual action required)
+# Advanced: Users can pre-install via system_dependencies=["build-essential"]
 RUN DEBIAN_FRONTEND=noninteractive apt-get update && apt-get install -y --no-install-recommends \
-    build-essential curl ca-certificates nala git \
+    curl ca-certificates nala git \
  && curl -LsSf https://astral.sh/uv/install.sh | sh \
  && cp ~/.local/bin/uv /usr/local/bin/uv \
  && chmod +x /usr/local/bin/uv \
diff --git a/Dockerfile-lb b/Dockerfile-lb
index 40c7999..2cc8952 100644
--- a/Dockerfile-lb
+++ b/Dockerfile-lb
@@ -17,8 +17,11 @@ RUN mkdir -p /root/.cache/apt/archives/partial \
  && echo 'Dir::Cache "/root/.cache/apt";' > /etc/apt/apt.conf.d/01cache
 
 # Install system dependencies and uv
+# Note: build-essential not pre-installed to reduce image size (400MB savings)
+# Automatic detection will install it when needed (no manual action required)
+# Advanced: Users can pre-install via system_dependencies=["build-essential"]
 RUN DEBIAN_FRONTEND=noninteractive apt-get update && apt-get install -y --no-install-recommends \
-    build-essential curl ca-certificates nala git \
+    curl ca-certificates nala git \
  && curl -LsSf https://astral.sh/uv/install.sh | sh \
  && cp ~/.local/bin/uv /usr/local/bin/uv \
  && chmod +x /usr/local/bin/uv \
diff --git a/Dockerfile-lb-cpu b/Dockerfile-lb-cpu
index af6ea3d..f39f321 100644
--- a/Dockerfile-lb-cpu
+++ b/Dockerfile-lb-cpu
@@ -12,8 +12,11 @@ RUN mkdir -p /root/.cache/apt/archives/partial \
  && echo 'Dir::Cache "/root/.cache/apt";' > /etc/apt/apt.conf.d/01cache
 
 # Install system dependencies and uv
+# Note: build-essential not pre-installed to reduce image size (400MB savings)
+# Automatic detection will install it when needed (no manual action required)
+# Advanced: Users can pre-install via system_dependencies=["build-essential"]
 RUN DEBIAN_FRONTEND=noninteractive apt-get update && apt-get install -y --no-install-recommends \
-    build-essential curl ca-certificates nala git \
+    curl ca-certificates nala git \
  && curl -LsSf https://astral.sh/uv/install.sh | sh \
  && cp ~/.local/bin/uv /usr/local/bin/uv \
  && chmod +x /usr/local/bin/uv \
diff --git a/src/dependency_installer.py b/src/dependency_installer.py
index 85c018d..cf23d17 100644
--- a/src/dependency_installer.py
+++ b/src/dependency_installer.py
@@ -21,7 +21,8 @@ def install_dependencies(
         self, packages: List[str], accelerate_downloads: bool = True
     ) -> FunctionResponse:
         """
-        Install Python packages using uv or regular pip
+        Install Python packages using uv or regular pip.
+        Automatically installs build-essential if compilation is required.
 
         Args:
             packages: List of package names or package specifications
@@ -48,13 +49,51 @@ def install_dependencies(
         operation_name = f"Installing Python packages ({'accelerated' if accelerate_downloads else 'standard'})"
 
         try:
-            return run_logged_subprocess(
+            result = run_logged_subprocess(
                 command=command,
                 logger=self.logger,
                 operation_name=operation_name,
                 timeout=300,
                 env=os.environ.copy(),
             )
+
+            # Check if installation failed due to missing compiler
+            if not result.success and self._needs_compilation(result):
+                self.logger.info(
+                    "Package compilation required but build tools missing. "
+                    "Auto-installing build-essential..."
+                )
+
+                # Install build-essential
+                build_result = self.install_system_dependencies(
+                    ["build-essential"], accelerate_downloads
+                )
+
+                if not build_result.success:
+                    return FunctionResponse(
+                        success=False,
+                        error=(
+                            f"Failed to install build tools: {build_result.error}\n\n"
+                            "Troubleshooting:\n"
+                            "1. Try manually specifying: system_dependencies=['build-essential']\n"
+                            "2. Check system package repositories are accessible\n"
+                            "3. Verify sufficient disk space for build tools (~400MB)"
+                        ),
+                        stdout=result.stdout,
+                    )
+
+                # Retry package installation with fresh timeout budget
+                self.logger.info("Retrying package installation with build tools...")
+                result = run_logged_subprocess(
+                    command=command,
+                    logger=self.logger,
+                    operation_name=f"{operation_name} (retry with build tools)",
+                    timeout=300,  # Fresh 300s timeout for retry (compilation may take longer)
+                    env=os.environ.copy(),
+                )
+
+            return result
+
         except Exception as e:
             return FunctionResponse(success=False, error=str(e))
 
@@ -117,6 +156,53 @@ def _check_nala_available(self) -> bool:
 
         return self._nala_available
 
+    def _needs_compilation(self, result: FunctionResponse) -> bool:
+        """
+        Detect if a package installation failure was due to missing compilation tools.
+
+        Args:
+            result: FunctionResponse from failed pip installation
+
+        Returns:
+            True if the error indicates missing compiler/build tools, False otherwise
+        """
+        # Common error patterns indicating missing compiler
+        # Note: Patterns are specific to avoid false positives on package names
+        error_indicators = [
+            "gcc: command not found",
+            "gcc: error",
+            "g++: command not found",
+            "g++: error",
+            "cc: command not found",
+            "cc: error",
+            "c++: command not found",
+            "c++: error",
+            "command 'gcc' failed",
+            "command 'g++' failed",
+            "command 'cc' failed",
+            "command 'c++' failed",
+            "unable to execute 'gcc'",
+            "unable to execute 'g++'",
+            "unable to execute 'cc'",
+            "unable to execute 'c++'",
+            "error: command 'gcc'",
+            "error: command 'cc'",
+            "no such file or directory: 'gcc'",
+            "no such file or directory: 'cc'",
+            "no such file or directory: 'g++'",
+            "no such file or directory: 'c++'",
+            "_distutils_hack",
+            "distutils.errors.compileerror",
+            "distutils.errors.distutilsexecerror",
+        ]
+
+        error_text = (result.error or "") + (result.stdout or "")
+        error_text_lower = error_text.lower()
+
+        return any(
+            indicator.lower() in error_text_lower for indicator in error_indicators
+        )
+
     def _is_docker_environment(self) -> bool:
         """
         Detect if we're running in a Docker container.
diff --git a/tests/unit/test_dependency_installer.py b/tests/unit/test_dependency_installer.py
index 5f132d4..a8181a9 100644
--- a/tests/unit/test_dependency_installer.py
+++ b/tests/unit/test_dependency_installer.py
@@ -295,3 +295,204 @@ def test_install_dependencies_timeout(self, mock_subprocess):
 
         assert result.success is False
         assert "timed out after 300 seconds" in result.error
+
+
+class TestCompilationAutoRetry:
+    """Test automatic build-essential installation when compilation needed."""
+
+    def setup_method(self):
+        """Setup for each test method."""
+        self.installer = DependencyInstaller()
+
+    def test_needs_compilation_gcc_not_found(self):
+        """Test detection of missing gcc compiler."""
+        result = FunctionResponse(
+            success=False,
+            error="error: command 'gcc' failed: No such file or directory",
+        )
+
+        assert self.installer._needs_compilation(result) is True
+
+    def test_needs_compilation_unable_to_execute_gcc(self):
+        """Test detection of unable to execute gcc."""
+        result = FunctionResponse(
+            success=False,
+            error="unable to execute 'gcc': No such file or directory",
+        )
+
+        assert self.installer._needs_compilation(result) is True
+
+    def test_needs_compilation_distutils_error(self):
+        """Test detection of distutils compilation errors."""
+        result = FunctionResponse(
+            success=False,
+            error="distutils.errors.CompileError: command 'gcc' failed",
+        )
+
+        assert self.installer._needs_compilation(result) is True
+
+    def test_needs_compilation_cc_command_failed(self):
+        """Test detection of cc command failure."""
+        result = FunctionResponse(
+            success=False, stdout="error: command 'cc' failed with exit code 1"
+        )
+
+        assert self.installer._needs_compilation(result) is True
+
+    def test_needs_compilation_gxx_missing(self):
+        """Test detection of missing g++ compiler."""
+        result = FunctionResponse(
+            success=False, error="unable to execute 'g++': No such file or directory"
+        )
+
+        assert self.installer._needs_compilation(result) is True
+
+    def test_needs_compilation_false_for_unrelated_error(self):
+        """Test that unrelated errors don't trigger compilation detection."""
+        result = FunctionResponse(
+            success=False, error="Network error: Could not find package"
+        )
+
+        assert self.installer._needs_compilation(result) is False
+
+    def test_needs_compilation_false_for_success(self):
+        """Test that successful installations don't trigger compilation detection."""
+        result = FunctionResponse(success=True, stdout="Successfully installed")
+
+        assert self.installer._needs_compilation(result) is False
+
+    @patch("platform.system")
+    @patch("dependency_installer.run_logged_subprocess")
+    def test_auto_retry_installs_build_essential_on_gcc_error(
+        self, mock_subprocess, mock_platform
+    ):
+        """Test auto-retry automatically installs build-essential when gcc missing."""
+        mock_platform.return_value = "Linux"
+
+        # First call: pip install fails with gcc error
+        # Second call: nala check (not available)
+        # Third call: apt-get update
+        # Fourth call: apt-get install build-essential
+        # Fifth call: pip install retry (succeeds)
+        mock_subprocess.side_effect = [
+            FunctionResponse(
+                success=False, error="error: command 'gcc' failed: No such file"
+            ),
+            FunctionResponse(success=False),  # nala not available
+            FunctionResponse(success=True, stdout="Updated"),  # apt-get update
+            FunctionResponse(
+                success=True, stdout="Installed build-essential"
+            ),  # apt-get install
+            FunctionResponse(success=True, stdout="Successfully installed package"),
+        ]
+
+        result = self.installer.install_dependencies(["some-package-needing-gcc"])
+
+        assert result.success is True
+        assert "Successfully installed package" in result.stdout
+        assert mock_subprocess.call_count == 5
+
+    @patch("dependency_installer.run_logged_subprocess")
+    def test_auto_retry_no_retry_for_non_compilation_errors(self, mock_subprocess):
+        """Test that non-compilation errors don't trigger auto-retry."""
+        # Pip install fails with network error (not compilation related)
+        mock_subprocess.return_value = FunctionResponse(
+            success=False, error="Network error: Could not fetch package"
+        )
+
+        result = self.installer.install_dependencies(["some-package"])
+
+        assert result.success is False
+        assert "Network error" in result.error
+        # Should only be called once (no retry)
+        assert mock_subprocess.call_count == 1
+
+    @patch("platform.system")
+    @patch("dependency_installer.run_logged_subprocess")
+    def test_auto_retry_fails_if_build_essential_install_fails(
+        self, mock_subprocess, mock_platform
+    ):
+        """Test that if build-essential installation fails, the error is returned."""
+        mock_platform.return_value = "Linux"
+
+        # First call: pip install fails with gcc error
+        # Second call: nala check (not available)
+        # Third call: apt-get update (fails)
+        mock_subprocess.side_effect = [
+            FunctionResponse(
+                success=False, error="error: command 'gcc' failed: No such file"
+            ),
+            FunctionResponse(success=False),  # nala not available
+            FunctionResponse(success=False, error="apt-get update failed"),
+        ]
+
+        result = self.installer.install_dependencies(["some-package-needing-gcc"])
+
+        assert result.success is False
+        assert "Failed to install build tools" in result.error
+
+    @patch("platform.system")
+    @patch("dependency_installer.run_logged_subprocess")
+    def test_auto_retry_with_nala_acceleration(self, mock_subprocess, mock_platform):
+        """Test auto-retry uses nala when available for build-essential installation."""
+        mock_platform.return_value = "Linux"
+
+        # First call: pip install fails with gcc error
+        # Second call: nala check (available)
+        # Third call: nala update
+        # Fourth call: nala install build-essential
+        # Fifth call: pip install retry (succeeds)
+        mock_subprocess.side_effect = [
+            FunctionResponse(
+                success=False, error="error: command 'gcc' failed: No such file"
+            ),
+            FunctionResponse(success=True, stdout="/usr/bin/nala"),  # nala available
+            FunctionResponse(success=True, stdout="Updated with nala"),
+            FunctionResponse(
+                success=True, stdout="Installed build-essential with nala"
+            ),
+            FunctionResponse(success=True, stdout="Successfully installed package"),
+        ]
+
+        result = self.installer.install_dependencies(["some-package-needing-gcc"])
+
+        assert result.success is True
+        assert "Successfully installed package" in result.stdout
+        assert mock_subprocess.call_count == 5
+
+    @patch("platform.system")
+    @patch("dependency_installer.run_logged_subprocess")
+    def test_auto_retry_succeeds_with_warnings_no_infinite_loop(
+        self, mock_subprocess, mock_platform
+    ):
+        """Test that warnings mentioning gcc in retry output don't trigger another retry."""
+        mock_platform.return_value = "Linux"
+
+        # First call: pip install fails with gcc error
+        # Second call: nala check (not available)
+        # Third call: apt-get update
+        # Fourth call: apt-get install build-essential
+        # Fifth call: pip install retry (succeeds but has warning mentioning gcc)
+        mock_subprocess.side_effect = [
+            FunctionResponse(
+                success=False,
+                error="error: command 'gcc' failed: No such file or directory",
+            ),
+            FunctionResponse(success=False),  # nala not available
+            FunctionResponse(success=True, stdout="Updated"),  # apt-get update
+            FunctionResponse(
+                success=True, stdout="Installed build-essential"
+            ),  # apt-get install
+            FunctionResponse(
+                success=True,
+                stdout="Successfully installed package\nWarning: gcc was used for compilation",
+            ),
+        ]
+
+        result = self.installer.install_dependencies(["some-package-needing-gcc"])
+
+        assert result.success is True
+        assert "Successfully installed package" in result.stdout
+        assert "Warning: gcc was used" in result.stdout
+        # Should only be called 5 times (no infinite retry loop)
+        assert mock_subprocess.call_count == 5