Propagate SSL/proxy environment to pip and uv subprocesses

rewrite-python/src/main/java/org/openrewrite/python/DependencyWorkspace.java

@@ -28,6 +28,7 @@
 import java.security.MessageDigest;
 import java.security.NoSuchAlgorithmException;
 import java.util.Base64;
+import java.util.Collections;
 import java.util.Comparator;
 import java.util.LinkedHashMap;
 import java.util.Map;
@@ -76,6 +77,18 @@ protected boolean removeEldestEntry(Map.Entry<String, Path> eldest) {
      * @return Path to the workspace directory containing .venv
      */
     static Path getOrCreateWorkspace(String pyprojectContent) {
+        return getOrCreateWorkspace(pyprojectContent, Collections.emptyMap());
+    }
+
+    /**
+     * Gets or creates a workspace directory for the given pyproject.toml content.
+     * Workspaces are cached by content hash to avoid repeated installations.
+     *
+     * @param pyprojectContent The complete pyproject.toml file content
+     * @param environment      additional environment variables for subprocess (e.g., SSL_CERT_FILE)
+     * @return Path to the workspace directory containing .venv
+     */
+    static Path getOrCreateWorkspace(String pyprojectContent, Map<String, String> environment) {
         String hash = hashContent(pyprojectContent);
 
         // Check in-memory cache
@@ -106,10 +119,10 @@ static Path getOrCreateWorkspace(String pyprojectContent) {
                 );
 
                 // Sync: creates .venv, generates uv.lock, and installs dependencies
-                runCommand(tempDir, "uv", "sync");
+                runCommand(tempDir, environment, "uv", "sync");
 
                 // Install ty for type stubs
-                runCommand(tempDir, "uv", "pip", "install", "ty");
+                runCommand(tempDir, environment, "uv", "pip", "install", "ty");
 
                 // Write workspace version for cache invalidation
                 Files.write(tempDir.resolve("version.txt"),
@@ -152,6 +165,21 @@ static Path getOrCreateWorkspace(String pyprojectContent) {
      */
     static @Nullable Path getOrCreateRequirementsWorkspace(String requirementsContent,
                                                             @Nullable Path originalFilePath) {
+        return getOrCreateRequirementsWorkspace(requirementsContent, originalFilePath, Collections.emptyMap());
+    }
+
+    /**
+     * Gets or creates a workspace directory for a requirements.txt file.
+     * Returns null (graceful degradation) when uv is unavailable.
+     *
+     * @param requirementsContent The complete requirements.txt content
+     * @param originalFilePath    The original file path on disk (supports -r includes), or null
+     * @param environment         additional environment variables for subprocess (e.g., SSL_CERT_FILE)
+     * @return Path to the workspace directory, or null if uv is unavailable
+     */
+    static @Nullable Path getOrCreateRequirementsWorkspace(String requirementsContent,
+                                                            @Nullable Path originalFilePath,
+                                                            Map<String, String> environment) {
         String uvPath = UvExecutor.findUvExecutable();
         if (uvPath == null) {
             return null;
@@ -180,7 +208,7 @@ static Path getOrCreateWorkspace(String pyprojectContent) {
 
             try {
                 // Create virtualenv
-                runCommandWithPath(tempDir, uvPath, "venv");
+                runCommandWithPath(tempDir, uvPath, environment, "venv");
 
                 // Install dependencies from requirements file
                 Path reqFile;
@@ -190,10 +218,10 @@ static Path getOrCreateWorkspace(String pyprojectContent) {
                     reqFile = tempDir.resolve("requirements.txt");
                     Files.write(reqFile, requirementsContent.getBytes(StandardCharsets.UTF_8));
                 }
-                runCommandWithPath(tempDir, uvPath, "pip", "install", "-r", reqFile.toString());
+                runCommandWithPath(tempDir, uvPath, environment, "pip", "install", "-r", reqFile.toString());
 
                 // Capture freeze output BEFORE installing ty
-                UvExecutor.RunResult freezeResult = UvExecutor.run(tempDir, uvPath, "pip", "freeze");
+                UvExecutor.RunResult freezeResult = UvExecutor.run(tempDir, uvPath, environment, "pip", "freeze");
                 if (freezeResult.isSuccess()) {
                     Files.write(
                             tempDir.resolve("freeze.txt"),
@@ -202,7 +230,7 @@ static Path getOrCreateWorkspace(String pyprojectContent) {
                 }
 
                 // Install ty for type stubs (after freeze so it's not in the dep model)
-                runCommandWithPath(tempDir, uvPath, "pip", "install", "ty");
+                runCommandWithPath(tempDir, uvPath, environment, "pip", "install", "ty");
 
                 // Write workspace version for cache invalidation
                 Files.write(tempDir.resolve("version.txt"),
@@ -243,6 +271,22 @@ static Path getOrCreateWorkspace(String pyprojectContent) {
      */
     public static @Nullable Path getOrCreateSetuptoolsWorkspace(String manifestContent,
                                                                 @Nullable Path projectDir) {
+        return getOrCreateSetuptoolsWorkspace(manifestContent, projectDir, Collections.emptyMap());
+    }
+
+    /**
+     * Gets or creates a workspace directory for a setuptools project (setup.cfg / setup.py).
+     * Uses {@code uv pip install <projectDir>} to install the project and its dependencies.
+     * Returns null (graceful degradation) when uv is unavailable.
+     *
+     * @param manifestContent The setup.cfg (or setup.py) content for hashing
+     * @param projectDir      The project directory to install from, or null
+     * @param environment     additional environment variables for subprocess (e.g., SSL_CERT_FILE)
+     * @return Path to the workspace directory, or null if uv is unavailable
+     */
+    public static @Nullable Path getOrCreateSetuptoolsWorkspace(String manifestContent,
+                                                                @Nullable Path projectDir,
+                                                                Map<String, String> environment) {
         String uvPath = UvExecutor.findUvExecutable();
         if (uvPath == null) {
             return null;
@@ -275,13 +319,13 @@ static Path getOrCreateWorkspace(String pyprojectContent) {
 
             try {
                 // Create virtualenv
-                runCommandWithPath(tempDir, uvPath, "venv");
+                runCommandWithPath(tempDir, uvPath, environment, "venv");
 
                 // Install from the project directory
-                runCommandWithPath(tempDir, uvPath, "pip", "install", projectDir.toString());
+                runCommandWithPath(tempDir, uvPath, environment, "pip", "install", projectDir.toString());
 
                 // Capture freeze output BEFORE installing ty
-                UvExecutor.RunResult freezeResult = UvExecutor.run(tempDir, uvPath, "pip", "freeze");
+                UvExecutor.RunResult freezeResult = UvExecutor.run(tempDir, uvPath, environment, "pip", "freeze");
                 if (freezeResult.isSuccess()) {
                     Files.write(
                             tempDir.resolve("freeze.txt"),
@@ -290,7 +334,7 @@ static Path getOrCreateWorkspace(String pyprojectContent) {
                 }
 
                 // Install ty for type stubs (after freeze so it's not in the dep model)
-                runCommandWithPath(tempDir, uvPath, "pip", "install", "ty");
+                runCommandWithPath(tempDir, uvPath, environment, "pip", "install", "ty");
 
                 // Write workspace version for cache invalidation
                 Files.write(tempDir.resolve("version.txt"),
@@ -335,14 +379,14 @@ private static boolean isRequirementsWorkspaceValid(Path workspaceDir) {
                 hasCurrentVersion(workspaceDir);
     }
 
-    private static void runCommandWithPath(Path dir, String uvPath, String... args) throws IOException, InterruptedException {
-        UvExecutor.RunResult result = UvExecutor.run(dir, uvPath, args);
+    private static void runCommandWithPath(Path dir, String uvPath, Map<String, String> environment, String... args) throws IOException, InterruptedException {
+        UvExecutor.RunResult result = UvExecutor.run(dir, uvPath, environment, args);
         if (!result.isSuccess()) {
             throw new RuntimeException("uv " + String.join(" ", args) + " failed with exit code: " + result.getExitCode());
         }
     }
 
-    private static void runCommand(Path dir, String... command) throws IOException, InterruptedException {
+    private static void runCommand(Path dir, Map<String, String> environment, String... command) throws IOException, InterruptedException {
         String uvPath = UvExecutor.findUvExecutable();
         if (uvPath == null) {
             throw new RuntimeException("uv is not installed. Install it with: pip install uv");
@@ -352,7 +396,7 @@ private static void runCommand(Path dir, String... command) throws IOException,
         String[] args = new String[command.length - 1];
         System.arraycopy(command, 1, args, 0, args.length);
 
-        UvExecutor.RunResult result = UvExecutor.run(dir, uvPath, args);
+        UvExecutor.RunResult result = UvExecutor.run(dir, uvPath, environment, args);
         if (!result.isSuccess()) {
             throw new RuntimeException(String.join(" ", command) + " failed with exit code: " + result.getExitCode());
         }

rewrite-python/src/main/java/org/openrewrite/python/RequirementsTxtParser.java

@@ -35,6 +35,8 @@
 import java.util.regex.Pattern;
 import java.util.stream.Stream;
 
+import static java.util.Collections.emptyMap;
+
 import static org.openrewrite.Tree.randomId;
 
 /**
@@ -50,6 +52,15 @@ public class RequirementsTxtParser implements Parser {
     private static final Pattern EXTRA_MARKER_PATTERN = Pattern.compile("\\bextra\\s*==");
 
     private final PlainTextParser plainTextParser = new PlainTextParser();
+    private final Map<String, String> subprocessEnvironment;
+
+    public RequirementsTxtParser() {
+        this(emptyMap());
+    }
+
+    public RequirementsTxtParser(Map<String, String> subprocessEnvironment) {
+        this.subprocessEnvironment = subprocessEnvironment;
+    }
 
     @Override
     public Stream<SourceFile> parseInputs(Iterable<Input> sources, @Nullable Path relativeTo, ExecutionContext ctx) {
@@ -64,7 +75,7 @@ public Stream<SourceFile> parseInputs(Iterable<Input> sources, @Nullable Path re
                 originalFilePath = relativeTo.resolve(text.getSourcePath());
             }
             Path workspace = DependencyWorkspace.getOrCreateRequirementsWorkspace(
-                    text.getText(), originalFilePath);
+                    text.getText(), originalFilePath, subprocessEnvironment);
             if (workspace == null) {
                 return sf;
             }

rewrite-python/src/main/java/org/openrewrite/python/SetupCfgParser.java

@@ -29,6 +29,7 @@
 import java.nio.file.Path;
 import java.util.Collections;
 import java.util.List;
+import java.util.Map;
 import java.util.stream.Stream;
 
 import static org.openrewrite.Tree.randomId;
@@ -41,6 +42,15 @@
 public class SetupCfgParser implements Parser {
 
     private final PlainTextParser plainTextParser = new PlainTextParser();
+    private final Map<String, String> subprocessEnvironment;
+
+    public SetupCfgParser() {
+        this(Collections.emptyMap());
+    }
+
+    public SetupCfgParser(Map<String, String> subprocessEnvironment) {
+        this.subprocessEnvironment = subprocessEnvironment;
+    }
 
     @Override
     public Stream<SourceFile> parseInputs(Iterable<Input> sources, @Nullable Path relativeTo, ExecutionContext ctx) {
@@ -56,7 +66,7 @@ public Stream<SourceFile> parseInputs(Iterable<Input> sources, @Nullable Path re
                 projectDir = filePath.getParent();
             }
             Path workspace = DependencyWorkspace.getOrCreateSetuptoolsWorkspace(
-                    text.getText(), projectDir);
+                    text.getText(), projectDir, subprocessEnvironment);
             if (workspace == null) {
                 return sf;
             }

rewrite-python/src/main/java/org/openrewrite/python/internal/UvExecutor.java

@@ -26,7 +26,9 @@
 import java.nio.file.Path;
 import java.nio.file.Paths;
 import java.util.ArrayList;
+import java.util.Collections;
 import java.util.List;
+import java.util.Map;
 import java.util.concurrent.TimeUnit;
 
 /**
@@ -37,7 +39,6 @@ public class UvExecutor {
 
     private static final long DEFAULT_TIMEOUT_SECONDS = 120;
     private static @Nullable String cachedUvPath;
-
     @Value
     public static class RunResult {
         boolean success;
@@ -55,12 +56,26 @@ public static class RunResult {
      * @return the run result
      */
     public static RunResult run(Path workDir, String uvPath, String... args) throws IOException, InterruptedException {
+        return run(workDir, uvPath, Collections.emptyMap(), args);
+    }
+
+    /**
+     * Run a uv command in the given directory with additional environment variables.
+     *
+     * @param workDir     the working directory
+     * @param uvPath      the path to the uv executable
+     * @param environment additional environment variables (e.g., SSL_CERT_FILE, HTTP_PROXY)
+     * @param args        the arguments to pass to uv
+     * @return the run result
+     */
+    public static RunResult run(Path workDir, String uvPath, Map<String, String> environment, String... args) throws IOException, InterruptedException {
         String[] command = new String[args.length + 1];
         command[0] = uvPath;
         System.arraycopy(args, 0, command, 1, args.length);
 
         ProcessBuilder pb = new ProcessBuilder(command);
         pb.directory(workDir.toFile());
+        pb.environment().putAll(environment);
         pb.redirectErrorStream(false);
 
         Process process = pb.start();

rewrite-python/src/main/java/org/openrewrite/python/internal/UvLockRegeneration.java

@@ -23,7 +23,9 @@
 import java.nio.charset.StandardCharsets;
 import java.nio.file.Files;
 import java.nio.file.Path;
+import java.util.Collections;
 import java.util.Comparator;
+import java.util.Map;
 
 /**
  * Utility for regenerating uv.lock files by running {@code uv lock} in a temporary directory.
@@ -53,7 +55,7 @@ public static Result failure(String errorMessage) {
      * @return a result containing the new lock file content, or an error message
      */
     public static Result regenerate(String pyprojectContent) {
-        return regenerate(pyprojectContent, null);
+        return regenerate(pyprojectContent, null, Collections.emptyMap());
     }
 
     /**
@@ -67,6 +69,21 @@ public static Result regenerate(String pyprojectContent) {
      * @return a result containing the new lock file content, or an error message
      */
     public static Result regenerate(String pyprojectContent, @Nullable String existingLockContent) {
+        return regenerate(pyprojectContent, existingLockContent, Collections.emptyMap());
+    }
+
+    /**
+     * Regenerate a uv.lock file from the given pyproject.toml content.
+     * When an existing lock file is provided it is seeded into the working
+     * directory so that {@code uv lock} performs a minimal update rather
+     * than re-resolving every dependency from scratch.
+     *
+     * @param pyprojectContent    the pyproject.toml content to lock
+     * @param existingLockContent the current uv.lock content, or {@code null}
+     * @param environment         additional environment variables for subprocess (e.g., SSL_CERT_FILE)
+     * @return a result containing the new lock file content, or an error message
+     */
+    public static Result regenerate(String pyprojectContent, @Nullable String existingLockContent, Map<String, String> environment) {
         String uvPath = UvExecutor.findUvExecutable();
         if (uvPath == null) {
             return Result.failure("uv is not installed. Install it with: pip install uv");
@@ -88,7 +105,7 @@ public static Result regenerate(String pyprojectContent, @Nullable String existi
                 );
             }
 
-            UvExecutor.RunResult runResult = UvExecutor.run(tempDir, uvPath, "lock");
+            UvExecutor.RunResult runResult = UvExecutor.run(tempDir, uvPath, environment, "lock");
             if (!runResult.isSuccess()) {
                 return Result.failure("uv lock failed (exit code " + runResult.getExitCode() + "): " + runResult.getStderr());
             }

rewrite-python/src/main/java/org/openrewrite/python/rpc/PythonRewriteRpc.java

@@ -273,7 +273,7 @@ public int characteristics() {
             return null;
         }
 
-        Path workspace = DependencyWorkspace.getOrCreateSetuptoolsWorkspace(source, projectPath);
+        Path workspace = DependencyWorkspace.getOrCreateSetuptoolsWorkspace(source, projectPath, commandEnv);
         if (workspace == null) {
             return null;
         }
@@ -334,11 +334,11 @@ private Stream<SourceFile> parseManifest(Path projectPath, @Nullable Path relati
         Path setupCfgPath = projectPath.resolve("setup.cfg");
         if (Files.exists(setupCfgPath)) {
             Parser.Input input = Parser.Input.fromFile(setupCfgPath);
-            return new SetupCfgParser().parseInputs(
+            return new SetupCfgParser(commandEnv).parseInputs(
                     Collections.singletonList(input), effectiveRelativeTo, ctx);
         }
 
-        RequirementsTxtParser reqsParser = new RequirementsTxtParser();
+        RequirementsTxtParser reqsParser = new RequirementsTxtParser(commandEnv);
         try (Stream<Path> entries = Files.list(projectPath)) {
             Path reqsPath = entries
                     .filter(p -> reqsParser.accept(p.getFileName()))
@@ -719,6 +719,7 @@ private void bootstrapOpenrewrite(Path pipPackagesPath, String version) {
                         "--target=" + pipPackagesPath.toAbsolutePath().normalize(),
                         "openrewrite==" + version
                 );
+                pb.environment().putAll(environment);
                 pb.redirectErrorStream(true);
                 if (log != null) {
                     File logFile = log.toAbsolutePath().normalize().toFile();