diff --git a/dist/setup/index.js b/dist/setup/index.js
index 4e3f2673..fd3d14a3 100644
--- a/dist/setup/index.js
+++ b/dist/setup/index.js
@@ -96164,13 +96164,32 @@ function useCpythonVersion(version, architecture, updateEnvironment, checkLatest
             core.addPath(installDir);
             core.addPath(_binDir);
             if (utils_1.IS_WINDOWS) {
-                // Add --user directory
-                // `installDir` from tool cache should look like $RUNNER_TOOL_CACHE/Python/<semantic version>/x64/
-                // So if `findLocalTool` succeeded above, we must have a conformant `installDir`
+                // Extract version details
                 const version = path.basename(path.dirname(installDir));
                 const major = semver.major(version);
                 const minor = semver.minor(version);
-                const userScriptsDir = path.join(process.env['APPDATA'] || '', 'Python', `Python${major}${minor}`, 'Scripts');
+                const basePath = process.env['APPDATA'] || '';
+                let versionSuffix = `${major}${minor}`;
+                // Append '-32' for x86 architecture if Python version is >= 3.10
+                if (architecture === 'x86' &&
+                    (major > 3 || (major === 3 && minor >= 10))) {
+                    versionSuffix += '-32';
+                }
+                else if (architecture === 'arm64') {
+                    versionSuffix += '-arm64';
+                }
+                // Append 't' for freethreaded builds
+                if (freethreaded) {
+                    versionSuffix += 't';
+                    if (architecture === 'x86-freethreaded') {
+                        versionSuffix += '-32';
+                    }
+                    else if (architecture === 'arm64-freethreaded') {
+                        versionSuffix += '-arm64';
+                    }
+                }
+                // Add user Scripts path
+                const userScriptsDir = path.join(basePath, 'Python', `Python${versionSuffix}`, 'Scripts');
                 core.addPath(userScriptsDir);
             }
             // On Linux and macOS, pip will create the --user directory and add it to PATH as needed.
diff --git a/src/find-python.ts b/src/find-python.ts
index ddb027cb..2e317d9c 100644
--- a/src/find-python.ts
+++ b/src/find-python.ts
@@ -49,8 +49,8 @@ export async function useCpythonVersion(
     // Use the freethreaded version if it was specified in the input, e.g., 3.13t
     freethreaded = true;
   }
-  core.debug(`Semantic version spec of ${version} is ${semanticVersionSpec}`);
 
+  core.debug(`Semantic version spec of ${version} is ${semanticVersionSpec}`);
   if (freethreaded) {
     // Free threaded versions use an architecture suffix like `x64-freethreaded`
     core.debug(`Using freethreaded version of ${semanticVersionSpec}`);
@@ -152,17 +152,36 @@ export async function useCpythonVersion(
     core.addPath(_binDir);
 
     if (IS_WINDOWS) {
-      // Add --user directory
-      // `installDir` from tool cache should look like $RUNNER_TOOL_CACHE/Python/<semantic version>/x64/
-      // So if `findLocalTool` succeeded above, we must have a conformant `installDir`
+      // Extract version details
       const version = path.basename(path.dirname(installDir));
       const major = semver.major(version);
       const minor = semver.minor(version);
 
+      const basePath = process.env['APPDATA'] || '';
+      let versionSuffix = `${major}${minor}`;
+      // Append '-32' for x86 architecture if Python version is >= 3.10
+      if (
+        architecture === 'x86' &&
+        (major > 3 || (major === 3 && minor >= 10))
+      ) {
+        versionSuffix += '-32';
+      } else if (architecture === 'arm64') {
+        versionSuffix += '-arm64';
+      }
+      // Append 't' for freethreaded builds
+      if (freethreaded) {
+        versionSuffix += 't';
+        if (architecture === 'x86-freethreaded') {
+          versionSuffix += '-32';
+        } else if (architecture === 'arm64-freethreaded') {
+          versionSuffix += '-arm64';
+        }
+      }
+      // Add user Scripts path
       const userScriptsDir = path.join(
-        process.env['APPDATA'] || '',
+        basePath,
         'Python',
-        `Python${major}${minor}`,
+        `Python${versionSuffix}`,
         'Scripts'
       );
       core.addPath(userScriptsDir);