diff --git a/packages/safe-chain/src/packagemanager/pip/runPipCommand.js b/packages/safe-chain/src/packagemanager/pip/runPipCommand.js
index e9f05c7..339876a 100644
--- a/packages/safe-chain/src/packagemanager/pip/runPipCommand.js
+++ b/packages/safe-chain/src/packagemanager/pip/runPipCommand.js
@@ -2,31 +2,13 @@ import { ui } from "../../environment/userInteraction.js";
 import { safeSpawn } from "../../utils/safeSpawn.js";
 import { mergeSafeChainProxyEnvironmentVariables } from "../../registryProxy/registryProxy.js";
 import { getCombinedCaBundlePath } from "../../registryProxy/certBundle.js";
-import { PIP_COMMAND, PIP3_COMMAND, PYTHON_COMMAND, PYTHON3_COMMAND } from "./pipSettings.js";
+import { PIP_COMMAND, PIP3_COMMAND } from "./pipSettings.js";
 import fs from "node:fs/promises";
 import fsSync from "node:fs";
 import os from "node:os";
 import path from "node:path";
 import ini from "ini";
 
-/**
- * Checks if this pip invocation should bypass safe-chain and spawn directly.
- * Returns true if the tool is python/python3 but NOT being run with -m pip/pip3.
- * @param {string} command - The command executable
- * @param {string[]} args - The arguments
- * @returns {boolean}
- */
-function shouldBypassSafeChain(command, args) {
-  if (command === PYTHON_COMMAND || command === PYTHON3_COMMAND) {
-    // Check if args start with -m pip
-    if (args.length >= 2 && args[0] === "-m" && (args[1] === PIP_COMMAND || args[1] === PIP3_COMMAND)) {
-      return false;
-    }
-    return true;
-  }
-  return false;
-}
-
 /**
  * Sets fallback CA bundle environment variables used by Python libraries.
  * These are applied in addition to the PIP_CONFIG_FILE to ensure all Python
@@ -73,23 +55,6 @@ function setFallbackCaBundleEnvironmentVariables(env, combinedCaPath) {
  * @returns {Promise<{status: number}>} Exit status of the pip command
  */
 export async function runPip(command, args) {
-  // Check if we should bypass safe-chain (python/python3 without -m pip)
-  if (shouldBypassSafeChain(command, args)) {
-    ui.writeVerbose(`Safe-chain: Bypassing safe-chain for non-pip invocation: ${command} ${args.join(" ")}`);
-    // Spawn the ORIGINAL command with ORIGINAL args
-    const { spawn } = await import("child_process");
-    return new Promise((_resolve) => {
-      const proc = spawn(command, args, { stdio: "inherit" });
-      proc.on("exit", (/** @type {number | null} */ code) => {
-        process.exit(code ?? 0);
-      });
-      proc.on("error", (/** @type {Error} */ err) => {
-        ui.writeError(`Error executing command: ${err.message}`);
-        process.exit(1);
-      });
-    });
-  }
-
   try {
     const env = mergeSafeChainProxyEnvironmentVariables(process.env);
 
diff --git a/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-fish.fish b/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-fish.fish
index 386144c..f538a6c 100644
--- a/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-fish.fish
+++ b/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-fish.fish
@@ -58,12 +58,22 @@ end
 
 # `python -m pip`, `python -m pip3`.
 function python
-    wrapSafeChainCommand "python" $argv
+    # Intercept only `python -m pip|pip3`; otherwise call real python
+    if test (count $argv) -ge 2; and test $argv[1] = "-m"; and (test $argv[2] = "pip" -o test $argv[2] = "pip3")
+        wrapSafeChainCommand "python" $argv
+    else
+        command python $argv
+    end
 end
 
 # `python3 -m pip`, `python3 -m pip3'.
 function python3
-    wrapSafeChainCommand "python3" $argv
+    # Intercept only `python3 -m pip|pip3`; otherwise call real python3
+    if test (count $argv) -ge 2; and test $argv[1] = "-m"; and (test $argv[2] = "pip" -o test $argv[2] = "pip3")
+        wrapSafeChainCommand "python3" $argv
+    else
+        command python3 $argv
+    end
 end
 
 function printSafeChainWarning
diff --git a/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-posix.sh b/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-posix.sh
index c71c741..240d37a 100644
--- a/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-posix.sh
+++ b/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-posix.sh
@@ -54,12 +54,22 @@ function poetry() {
 
 # `python -m pip`, `python -m pip3`.
 function python() {
-  wrapSafeChainCommand "python" "$@"
+  # Intercept only `python -m pip|pip3`; otherwise run the real python to avoid loops/shadowing
+  if [[ "$1" == "-m" && ( "$2" == "pip" || "$2" == "pip3" ) ]]; then
+    wrapSafeChainCommand "python" "$@"
+  else
+    command python "$@"
+  fi
 }
 
 # `python3 -m pip`, `python3 -m pip3'.
 function python3() {
-  wrapSafeChainCommand "python3" "$@"
+  # Intercept only `python3 -m pip|pip3`; otherwise run the real python3
+  if [[ "$1" == "-m" && ( "$2" == "pip" || "$2" == "pip3" ) ]]; then
+    wrapSafeChainCommand "python3" "$@"
+  else
+    command python3 "$@"
+  fi
 }
 
 function printSafeChainWarning() {
diff --git a/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-pwsh.ps1 b/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-pwsh.ps1
index 168556a..d191dfc 100644
--- a/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-pwsh.ps1
+++ b/packages/safe-chain/src/shell-integration/startup-scripts/include-python/init-pwsh.ps1
@@ -56,12 +56,22 @@ function poetry {
 
 # `python -m pip`, `python -m pip3`.
 function python {
-    Invoke-WrappedCommand 'python' $args
+    # Intercept only `python -m pip|pip3`; otherwise invoke real python
+    if (($args.Length -ge 2) -and ($args[0] -eq '-m') -and (($args[1] -eq 'pip') -or ($args[1] -eq 'pip3'))) {
+        Invoke-WrappedCommand 'python' $args
+    } else {
+        Invoke-RealCommand 'python' $args
+    }
 }
 
 # `python3 -m pip`, `python3 -m pip3'.
 function python3 {
-    Invoke-WrappedCommand 'python3' $args
+    # Intercept only `python3 -m pip|pip3`; otherwise invoke real python3
+    if (($args.Length -ge 2) -and ($args[0] -eq '-m') -and (($args[1] -eq 'pip') -or ($args[1] -eq 'pip3'))) {
+        Invoke-WrappedCommand 'python3' $args
+    } else {
+        Invoke-RealCommand 'python3' $args
+    }
 }
 
 
diff --git a/test/e2e/DockerTestContainer.js b/test/e2e/DockerTestContainer.js
index ec1af3c..d3c6166 100644
--- a/test/e2e/DockerTestContainer.js
+++ b/test/e2e/DockerTestContainer.js
@@ -16,20 +16,22 @@ const yarnVersion = process.env.YARN_VERSION || "latest";
 const pnpmVersion = process.env.PNPM_VERSION || "latest";
 
 export class DockerTestContainer {
-  constructor() {
+  constructor(profile = "default") {
     this.containerName = `safe-chain-test-${Math.random()
       .toString(36)
       .substring(2, 15)}`;
     this.isRunning = false;
+    this.profile = profile;
   }
 
-  static buildImage() {
+  static buildImage(profile = "default") {
     try {
       const buildArgs = [
         `--build-arg NODE_VERSION=${nodeVersion}`,
         `--build-arg NPM_VERSION=${npmVersion}`,
         `--build-arg YARN_VERSION=${yarnVersion}`,
         `--build-arg PNPM_VERSION=${pnpmVersion}`,
+        profile === "pyenv" ? "--build-arg ENABLE_PYENV=true" : "",
       ].join(" ");
 
       execSync(
diff --git a/test/e2e/Dockerfile b/test/e2e/Dockerfile
index c8d9c9c..8bb1b55 100644
--- a/test/e2e/Dockerfile
+++ b/test/e2e/Dockerfile
@@ -26,6 +26,7 @@ ARG NPM_VERSION=latest
 ARG YARN_VERSION=latest
 ARG PNPM_VERSION=latest
 ARG PYTHON_VERSION=3
+ARG ENABLE_PYENV=false
 
 SHELL ["/bin/bash", "-c"]
 ENV BASH_ENV=~/.bashrc
@@ -84,3 +85,10 @@ RUN npm install -g /pkgs/*.tgz
 WORKDIR /testapp
 RUN npm init -y
 
+# Optional: install pyenv and set a managed Python version when enabled
+RUN if [ "$ENABLE_PYENV" = "true" ]; then \
+            apt-get update && apt-get install -y git build-essential libssl-dev zlib1g-dev libbz2-dev libreadline-dev libsqlite3-dev libffi-dev && \
+            git clone https://github.com/pyenv/pyenv.git /root/.pyenv && \
+            bash -lc 'export PYENV_ROOT=/root/.pyenv; export PATH="$PYENV_ROOT/bin:$PATH"; eval "$(pyenv init -)"; pyenv install 3.12.3; pyenv global 3.12.3'; \
+        fi
+
diff --git a/test/e2e/pip.e2e.spec.js b/test/e2e/pip.e2e.spec.js
index e02d1b3..8afae22 100644
--- a/test/e2e/pip.e2e.spec.js
+++ b/test/e2e/pip.e2e.spec.js
@@ -569,6 +569,137 @@ describe("E2E: pip coverage", () => {
     );
   });
 
+  it(`python3 --version completes quickly (no recursion/loop)`, async () => {
+    const shell = await container.openShell("zsh");
+    const start = Date.now();
+    const result = await shell.runCommand("python3 --version");
+    const durationMs = Date.now() - start;
+
+    assert.ok(
+      durationMs < 3000,
+      `Command should complete quickly. Took ${durationMs}ms. Output was:\n${result.output}`
+    );
+    assert.ok(
+      result.output.match(/Python 3\.\d+\.\d+/),
+      `Should output Python version. Output was:\n${result.output}`
+    );
+  });
+
+  it(`alias python=python3 still bypasses and is fast`, async () => {
+    const shell = await container.openShell("zsh");
+    await shell.runCommand("alias python=python3");
+
+    const start = Date.now();
+    const result = await shell.runCommand("python --version");
+    const durationMs = Date.now() - start;
+
+    assert.ok(
+      durationMs < 3000,
+      `Command should complete quickly. Took ${durationMs}ms. Output was:\n${result.output}`
+    );
+    assert.ok(
+      result.output.match(/Python 3\.\d+\.\d+/),
+      `Should output Python 3 version via alias. Output was:\n${result.output}`
+    );
+    assert.ok(
+      !result.output.includes("Safe-chain"),
+      `Non-pip alias should bypass safe-chain. Output was:\n${result.output}`
+    );
+  });
+
+  it(`alias python=python3, python -m pip goes through safe-chain`, async () => {
+    const shell = await container.openShell("zsh");
+    await shell.runCommand("alias python=python3");
+
+    const start = Date.now();
+    const result = await shell.runCommand(
+      "python -m pip install --break-system-packages certifi --safe-chain-logging=verbose"
+    );
+    const durationMs = Date.now() - start;
+
+    assert.ok(
+      durationMs < 10000,
+      `Install should not hang or loop under alias. Took ${durationMs}ms. Output was:\n${result.output}`
+    );
+    assert.ok(
+      result.output.includes("Safe-chain") ||
+        result.output.includes("no malware found"),
+      `pip flow SHOULD be protected even with alias. Output was:\n${result.output}`
+    );
+  });
+
+  // Shadowing function tests: user-defined shell function overrides wrapper
+  it(`function python(){ python3 "$@"; } bypasses non-pip and is fast`, async () => {
+    const shell = await container.openShell("zsh");
+    await shell.runCommand('function python(){ python3 "$@"; }');
+
+    const start = Date.now();
+    const result = await shell.runCommand("python --version");
+    const durationMs = Date.now() - start;
+
+    assert.ok(
+      durationMs < 3000,
+      `Command should complete quickly under shadowing function. Took ${durationMs}ms. Output was:\n${result.output}`
+    );
+    assert.ok(
+      result.output.match(/Python 3\.\d+\.\d+/),
+      `Should output Python 3 version via shadowing function. Output was:\n${result.output}`
+    );
+    assert.ok(
+      !result.output.includes("Safe-chain"),
+      `Non-pip via shadowing function should bypass safe-chain. Output was:\n${result.output}`
+    );
+  });
+
+  it(`function python(){ python3 "$@"; } with python -m pip is protected`, async () => {
+    const shell = await container.openShell("zsh");
+    await shell.runCommand('function python(){ python3 "$@"; }');
+
+    const start = Date.now();
+    const result = await shell.runCommand(
+      "python -m pip install --break-system-packages certifi --safe-chain-logging=verbose"
+    );
+    const durationMs = Date.now() - start;
+
+    assert.ok(
+      durationMs < 10000,
+      `Install should not hang or loop under shadowing function. Took ${durationMs}ms. Output was:\n${result.output}`
+    );
+    assert.ok(
+      result.output.includes("Safe-chain") ||
+        result.output.includes("no malware found"),
+      `pip flow SHOULD be protected even with shadowing function. Output was:\n${result.output}`
+    );
+  });
+
+  it(`shadow function + python -m pip blocks malware`, async () => {
+    const shell = await container.openShell("zsh");
+    await shell.runCommand('function python(){ python3 "$@"; }');
+
+    const result = await shell.runCommand(
+      "python -m pip install --break-system-packages safe-chain-pi-test"
+    );
+
+    assert.ok(
+      result.output.includes("blocked 1 malicious package downloads:"),
+      `Should block malware under shadow function. Output was:\n${result.output}`
+    );
+    assert.ok(
+      result.output.includes("safe_chain_pi_test@0.0.1"),
+      `Should identify malware package. Output was:\n${result.output}`
+    );
+    assert.ok(
+      result.output.includes("Exiting without installing malicious packages."),
+      `Should refuse installation. Output was:\n${result.output}`
+    );
+
+    const listResult = await shell.runCommand("python -m pip list");
+    assert.ok(
+      !listResult.output.includes("safe-chain-pi-test"),
+      `Malicious package should not be installed. Output was:\n${listResult.output}`
+    );
+  });
+
   it(`python --version should bypass safe-chain and work normally`, async () => {
     const shell = await container.openShell("zsh");
     const result = await shell.runCommand("python --version");
@@ -817,6 +948,25 @@ describe("E2E: pip coverage", () => {
     );
   });
 
+  it(`python3 -m pip completes quickly and shows protection`, async () => {
+    const shell = await container.openShell("zsh");
+    const start = Date.now();
+    const result = await shell.runCommand(
+      "python3 -m pip install --break-system-packages certifi --safe-chain-logging=verbose"
+    );
+    const durationMs = Date.now() - start;
+
+    assert.ok(
+      durationMs < 10000,
+      `Install should not hang or loop. Took ${durationMs}ms. Output was:\n${result.output}`
+    );
+    assert.ok(
+      result.output.includes("Safe-chain") ||
+        result.output.includes("no malware found"),
+      `python3 -m pip SHOULD go through safe-chain. Output was:\n${result.output}`
+    );
+  });
+
   it(`python3 -m pip3 DOES go through safe-chain (sanity check)`, async () => {
     const shell = await container.openShell("zsh");
     const result = await shell.runCommand(
diff --git a/test/e2e/pyenv.e2e.spec.js b/test/e2e/pyenv.e2e.spec.js
new file mode 100644
index 0000000..fdbe172
--- /dev/null
+++ b/test/e2e/pyenv.e2e.spec.js
@@ -0,0 +1,155 @@
+import { describe, it, before, after } from "node:test";
+import assert from "node:assert";
+import { DockerTestContainer } from "./DockerTestContainer.js";
+
+let hasPyenv = false;
+
+describe("E2E: pyenv wrappers only intercept -m pip", () => {
+  let c;
+
+  before(async () => {
+    DockerTestContainer.buildImage("pyenv");
+    c = new DockerTestContainer("pyenv");
+    await c.start();
+    const sh = await c.openShell("bash");
+    // Ensure pyenv is on PATH and shims initialized for this shell
+    await sh.runCommand(
+      'export PYENV_ROOT=/root/.pyenv; export PATH="$PYENV_ROOT/bin:$PATH"; eval "$(pyenv init -)" || true'
+    );
+    await sh.runCommand("pip3 cache purge >/dev/null 2>&1 || true");
+    // Assert pyenv is installed and active
+    const v = await sh.runCommand("pyenv --version || echo MISSING");
+    hasPyenv = /pyenv [0-9]/.test(v);
+    if (hasPyenv) {
+      const versions = await sh.runCommand("pyenv versions || true");
+      // Non-fatal check: ensure at least one version appears
+      assert.match(versions, /(system|\d+\.\d+)/, "pyenv versions should list entries");
+      const whichPy = await sh.runCommand("pyenv which python || true");
+      assert.match(whichPy, /\.pyenv\/versions\//, "pyenv which python should point to pyenv version dir");
+    }
+  });
+
+  it("pyenv local sets project-specific version", async () => {
+    if (!hasPyenv) return;
+    const sh = await c.openShell("bash");
+    await sh.runCommand("mkdir -p /work/localtest && cd /work/localtest && pyenv local 3.12.3");
+    const inside = await sh.runCommand("cd /work/localtest && python --version 2>&1");
+    assert.match(inside, /Python 3\.12\./);
+    const outside = await sh.runCommand("cd / && pyenv version && python --version 2>&1");
+    assert.notMatch(outside, /3\.12\./, "outside dir should not be forced to 3.12 by local file");
+  });
+
+  it("pyenv shell overrides version for current session", async () => {
+    if (!hasPyenv) return;
+    const sh = await c.openShell("bash");
+    // Set shell-specific version
+    await sh.runCommand("pyenv shell 3.12.3");
+    const v1 = await sh.runCommand("pyenv version");
+    assert.match(v1, /3\.12\.3 \(set by PYENV_VERSION/);
+    const p1 = await sh.runCommand("python --version 2>&1");
+    assert.match(p1, /Python 3\.12\./);
+    // Unset and verify it reverts
+    await sh.runCommand("pyenv shell --unset");
+    const v2 = await sh.runCommand("pyenv version");
+    assert.match(v2, /system \(set by .*\.pyenv\/version\)/);
+  });
+
+  after(async () => {
+    await c.stop();
+  });
+
+  it("python --version bypasses and succeeds", async () => {
+    const sh = await c.openShell("bash");
+    await sh.runCommand("safe-chain setup --include-python >/dev/null 2>&1 || true");
+    const res = await sh.runCommand("python --version 2>&1; echo EXIT:$?\n");
+    assert.ok(/Python\s+\d+\.\d+\.\d+/.test(res.output), `version missing: ${res.output}`);
+    assert.ok(res.output.includes("EXIT:0"), `exit not 0: ${res.output}`);
+  });
+
+  it("python3 --version bypasses and succeeds", async () => {
+    const sh = await c.openShell("bash");
+    const res = await sh.runCommand("python3 --version 2>&1; echo EXIT:$?\n");
+    assert.ok(/Python\s+3\./.test(res.output), `version missing: ${res.output}`);
+    assert.ok(res.output.includes("EXIT:0"), `exit not 0: ${res.output}`);
+  });
+
+  it("shadowing function: command python succeeds (explicit bypass)", async () => {
+    const sh = await c.openShell("bash");
+    await sh.runCommand("python() { return 1; }; export -f python");
+    const res = await sh.runCommand("type -a python; command python --version 2>&1; echo EXIT:$?\n");
+    assert.ok(/Python\s+\d+\.\d+\.\d+/.test(res.output), `version missing: ${res.output}`);
+    assert.ok(res.output.includes("EXIT:0"), `exit not 0: ${res.output}`);
+  });
+
+  it("python -m pip install succeeds under wrappers", async () => {
+    const sh = await c.openShell("bash");
+    await sh.runCommand("pip3 cache purge >/dev/null 2>&1 || true");
+    const res = await sh.runCommand("python3 -m pip install --break-system-packages certifi 2>&1\n");
+    assert.ok(res.output.match(/Successfully installed|Requirement already satisfied/), `pip install did not succeed: ${res.output}`);
+  });
+
+  it("python -m pip blocks malware under pyenv-style shadow", async () => {
+    const sh = await c.openShell("bash");
+    await sh.runCommand("safe-chain setup --include-python >/dev/null 2>&1 || true");
+    await sh.runCommand("pip3 cache purge >/dev/null 2>&1 || true");
+    // Emulate pyenv-style function forwarding
+    await sh.runCommand('python() { python3 "$@"; }; export -f python');
+
+    const res = await sh.runCommand("python -m pip install --break-system-packages safe-chain-pi-test 2>&1\n");
+    assert.ok(
+      res.output.includes("blocked 1 malicious package downloads:"),
+      `Should block malware. Output:\n${res.output}`
+    );
+    assert.ok(
+      res.output.includes("safe_chain_pi_test@0.0.1"),
+      `Should identify malware package. Output:\n${res.output}`
+    );
+    assert.ok(
+      res.output.includes("Exiting without installing malicious packages."),
+      `Should refuse installation. Output:\n${res.output}`
+    );
+
+    const list = await sh.runCommand("python -m pip list 2>&1\n");
+    assert.ok(
+      !list.output.includes("safe-chain-pi-test"),
+      `Malicious package should not be installed. Output:\n${list.output}`
+    );
+  });
+
+  it("python -m pip works and installs (no shadow)", async () => {
+    const sh = await c.openShell("bash");
+    await sh.runCommand("safe-chain setup --include-python >/dev/null 2>&1 || true");
+    await sh.runCommand("pip3 cache purge >/dev/null 2>&1 || true");
+
+    const res = await sh.runCommand("python -m pip install --break-system-packages certifi --safe-chain-logging=verbose 2>&1\n");
+    assert.ok(
+      res.output.match(/Successfully installed|Requirement already satisfied/),
+      `pip install should succeed. Output:\n${res.output}`
+    );
+  });
+
+  it("pip3 download works and scans (no shadow)", async () => {
+    const sh = await c.openShell("bash");
+    await sh.runCommand("safe-chain setup --include-python >/dev/null 2>&1 || true");
+    await sh.runCommand("pip3 cache purge >/dev/null 2>&1 || true");
+
+    const res = await sh.runCommand("pip3 download requests --safe-chain-logging=verbose 2>&1\n");
+    assert.ok(
+      res.output.includes("no malware found."),
+      `Download should be scanned. Output:\n${res.output}`
+    );
+  });
+
+  it("pip3 wheel works and proxies registry (no shadow)", async () => {
+    const sh = await c.openShell("bash");
+    await sh.runCommand("safe-chain setup --include-python >/dev/null 2>&1 || true");
+    await sh.runCommand("pip3 cache purge >/dev/null 2>&1 || true");
+
+    const res = await sh.runCommand("pip3 wheel requests --safe-chain-logging=verbose 2>&1\n");
+    assert.ok(
+      res.output.includes("Safe-chain: Set up MITM tunnel") ||
+        res.output.includes("Finished proxying request"),
+      `Wheel should route via proxy. Output:\n${res.output}`
+    );
+  });
+});