diff --git a/nifi-nar-bundles/nifi-py4j-bundle/nifi-py4j-bridge/src/main/java/org/apache/nifi/py4j/PythonProcess.java b/nifi-nar-bundles/nifi-py4j-bundle/nifi-py4j-bridge/src/main/java/org/apache/nifi/py4j/PythonProcess.java
index f34199b5bc..3cfb2b30f4 100644
--- a/nifi-nar-bundles/nifi-py4j-bundle/nifi-py4j-bridge/src/main/java/org/apache/nifi/py4j/PythonProcess.java
+++ b/nifi-nar-bundles/nifi-py4j-bundle/nifi-py4j-bridge/src/main/java/org/apache/nifi/py4j/PythonProcess.java
@@ -227,10 +227,7 @@ public class PythonProcess {
     private Process launchPythonProcess(final int listeningPort, final String authToken) throws IOException {
         final File pythonFrameworkDirectory = processConfig.getPythonFrameworkDirectory();
         final File pythonApiDirectory = new File(pythonFrameworkDirectory.getParentFile(), "api");
-        final File pythonCmdFile = new File(processConfig.getPythonCommand());
-        final String pythonCmd = pythonCmdFile.getName();
-        final File pythonCommandFile = new File(virtualEnvHome, "bin/" + pythonCmd);
-        final String pythonCommand = pythonCommandFile.getAbsolutePath();
+        final String pythonCommand = resolvePythonCommand();
 
         final File controllerPyFile = new File(pythonFrameworkDirectory, PYTHON_CONTROLLER_FILENAME);
         final ProcessBuilder processBuilder = new ProcessBuilder();
@@ -256,7 +253,7 @@ public class PythonProcess {
         processBuilder.environment().put("JAVA_PORT", String.valueOf(listeningPort));
         processBuilder.environment().put("ENV_HOME", virtualEnvHome.getAbsolutePath());
         processBuilder.environment().put("PYTHONPATH", pythonPath);
-        processBuilder.environment().put("PYTHON_CMD", pythonCommandFile.getAbsolutePath());
+        processBuilder.environment().put("PYTHON_CMD", pythonCommand);
         processBuilder.environment().put("AUTH_TOKEN", authToken);
 
         // Redirect error stream to standard output stream
@@ -267,6 +264,27 @@ public class PythonProcess {
         return processBuilder.start();
     }
 
+    String resolvePythonCommand() throws IOException {
+        final File pythonCmdFile = new File(processConfig.getPythonCommand());
+        final String pythonCmd = pythonCmdFile.getName();
+
+        // Find command directories according to standard Python venv conventions
+        final File[] virtualEnvDirectories = virtualEnvHome.listFiles((file, name) -> file.isDirectory() && (name.equals("bin") || name.equals("Scripts")));
+
+        final String commandExecutableDirectory;
+        if (virtualEnvDirectories == null || virtualEnvDirectories.length == 0) {
+            throw new IOException("Python binary directory could not be found in " + virtualEnvHome);
+        } else if( virtualEnvDirectories.length == 1) {
+            commandExecutableDirectory = virtualEnvDirectories[0].getName();
+        } else {
+            // Default to bin directory for macOS and Linux
+            commandExecutableDirectory = "bin";
+        }
+
+        final File pythonCommandFile = new File(virtualEnvHome, commandExecutableDirectory + File.separator + pythonCmd);
+        return pythonCommandFile.getAbsolutePath();
+    }
+
 
     private void setupEnvironment() throws IOException {
         final File environmentCreationCompleteFile = new File(virtualEnvHome, "env-creation-complete.txt");
diff --git a/nifi-nar-bundles/nifi-py4j-bundle/nifi-py4j-bridge/src/test/java/org/apache/nifi/py4j/PythonProcessTest.java b/nifi-nar-bundles/nifi-py4j-bundle/nifi-py4j-bridge/src/test/java/org/apache/nifi/py4j/PythonProcessTest.java
new file mode 100644
index 0000000000..4a1ad32638
--- /dev/null
+++ b/nifi-nar-bundles/nifi-py4j-bundle/nifi-py4j-bridge/src/test/java/org/apache/nifi/py4j/PythonProcessTest.java
@@ -0,0 +1,109 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one or more
+ * contributor license agreements.  See the NOTICE file distributed with
+ * this work for additional information regarding copyright ownership.
+ * The ASF licenses this file to You under the Apache License, Version 2.0
+ * (the "License"); you may not use this file except in compliance with
+ * the License.  You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package org.apache.nifi.py4j;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+import static org.junit.jupiter.api.Assertions.assertTrue;
+import static org.mockito.Mockito.when;
+
+import java.io.File;
+import java.io.IOException;
+
+import org.apache.nifi.python.ControllerServiceTypeLookup;
+import org.apache.nifi.python.PythonProcessConfig;
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.ExtendWith;
+import org.junit.jupiter.api.io.CleanupMode;
+import org.junit.jupiter.api.io.TempDir;
+import org.mockito.Mock;
+import org.mockito.junit.jupiter.MockitoExtension;
+
+@ExtendWith(MockitoExtension.class)
+class PythonProcessTest {
+
+    private static final String UNIX_BIN_DIR = "bin";
+
+    private static final String WINDOWS_SCRIPTS_DIR = "Scripts";
+
+    private static final String PYTHON_CMD = "python";
+
+    private PythonProcess pythonProcess;
+
+    @TempDir(cleanup = CleanupMode.ON_SUCCESS)
+    private File virtualEnvHome;
+
+    @Mock
+    private PythonProcessConfig pythonProcessConfig;
+
+    @Mock
+    private ControllerServiceTypeLookup controllerServiceTypeLookup;
+
+    @BeforeEach
+    public void setUp() {
+        this.pythonProcess = new PythonProcess(this.pythonProcessConfig, this.controllerServiceTypeLookup, virtualEnvHome, "Controller", "Controller");
+    }
+
+    @Test
+    void testResolvePythonCommandWindows() throws IOException {
+        final File scriptsDir = new File(virtualEnvHome, WINDOWS_SCRIPTS_DIR);
+        assertTrue(scriptsDir.mkdir());
+
+        when(pythonProcessConfig.getPythonCommand()).thenReturn(PYTHON_CMD);
+        final String result = this.pythonProcess.resolvePythonCommand();
+
+        final String expected = getExpectedBinaryPath(WINDOWS_SCRIPTS_DIR);
+        assertEquals(expected, result);
+    }
+
+    @Test
+    void testResolvePythonCommandUnix() throws IOException {
+        final File binDir = new File(virtualEnvHome, UNIX_BIN_DIR);
+        assertTrue(binDir.mkdir());
+
+        when(pythonProcessConfig.getPythonCommand()).thenReturn(PYTHON_CMD);
+        final String result = this.pythonProcess.resolvePythonCommand();
+
+        final String expected = getExpectedBinaryPath(UNIX_BIN_DIR);
+        assertEquals(expected, result);
+    }
+
+    @Test
+    void testResolvePythonCommandPreferBin() throws IOException {
+        final File binDir = new File(virtualEnvHome, UNIX_BIN_DIR);
+        assertTrue(binDir.mkdir());
+        final File scriptsDir = new File(virtualEnvHome, WINDOWS_SCRIPTS_DIR);
+        assertTrue(scriptsDir.mkdir());
+
+        when(pythonProcessConfig.getPythonCommand()).thenReturn(PYTHON_CMD);
+        final String result = this.pythonProcess.resolvePythonCommand();
+
+        final String expected = getExpectedBinaryPath(UNIX_BIN_DIR);
+        assertEquals(expected, result);
+    }
+
+    @Test
+    void testResolvePythonCommandNone() {
+        when(pythonProcessConfig.getPythonCommand()).thenReturn(PYTHON_CMD);
+        assertThrows(IOException.class, ()-> this.pythonProcess.resolvePythonCommand());
+    }
+
+    private String getExpectedBinaryPath(String binarySubDirectoryName) {
+        return this.virtualEnvHome.getAbsolutePath() + File.separator + binarySubDirectoryName + File.separator + PYTHON_CMD;
+    }
+}