diff --git a/src/extension/debugger/configuration/resolvers/helper.ts b/src/extension/debugger/configuration/resolvers/helper.ts
index 6791bded..59258381 100644
--- a/src/extension/debugger/configuration/resolvers/helper.ts
+++ b/src/extension/debugger/configuration/resolvers/helper.ts
@@ -4,6 +4,7 @@
 
 'use strict';
 
+import * as path from 'path';
 import { PYTHON_LANGUAGE } from '../../../common/constants';
 import { getSearchPathEnvVarNames } from '../../../common/utils/exec';
 import { EnvironmentVariables } from '../../../common/variables/types';
@@ -11,8 +12,38 @@ import { getActiveTextEditor } from '../../../common/vscodeapi';
 import { LaunchRequestArguments } from '../../../types';
 import * as envParser from '../../../common/variables/environment';
 
+function getSearchPathEnvVar(vars: EnvironmentVariables, names: ('Path' | 'PATH')[]): string | undefined {
+    return names.map((name) => vars[name]).find((value) => typeof value === 'string' && value.length > 0);
+}
+
+function normalizeSearchPathEnvVar(env: EnvironmentVariables, names: ('Path' | 'PATH')[]) {
+    const [pathVariableName, ...alternatePathVariableNames] = names;
+    for (const alternatePathVariableName of alternatePathVariableNames) {
+        const alternateValue = env[alternatePathVariableName];
+        if (typeof alternateValue !== 'string' || alternateValue.length === 0) {
+            delete env[alternatePathVariableName];
+            continue;
+        }
+
+        const currentValue = env[pathVariableName];
+        if (typeof currentValue === 'string' && currentValue.length > 0) {
+            const currentSegments = new Set(currentValue.split(path.delimiter).filter((item) => item.length > 0));
+            const alternateSegments = alternateValue
+                .split(path.delimiter)
+                .filter((item) => item.length > 0 && !currentSegments.has(item));
+            if (alternateSegments.length > 0) {
+                env[pathVariableName] = [currentValue, ...alternateSegments].join(path.delimiter);
+            }
+        } else {
+            env[pathVariableName] = alternateValue;
+        }
+        delete env[alternatePathVariableName];
+    }
+}
+
 export async function getDebugEnvironmentVariables(args: LaunchRequestArguments): Promise<EnvironmentVariables> {
-    const pathVariableName = getSearchPathEnvVarNames()[0];
+    const pathVariableNames = getSearchPathEnvVarNames();
+    const pathVariableName = pathVariableNames[0];
 
     // Merge variables from both .env file and env json variables.
     const debugLaunchEnvVars: Record<string, string> =
@@ -20,20 +51,29 @@ export async function getDebugEnvironmentVariables(args: LaunchRequestArguments)
             ? ({ ...args.env } as Record<string, string>)
             : ({} as Record<string, string>);
     const envFileVars = await envParser.parseFile(args.envFile, debugLaunchEnvVars);
+    normalizeSearchPathEnvVar(debugLaunchEnvVars, pathVariableNames);
     const env = envFileVars ? { ...envFileVars } : {};
+    normalizeSearchPathEnvVar(env, pathVariableNames);
 
     // "overwrite: true" to ensure that debug-configuration env variable values
     // take precedence over env file.
     envParser.mergeVariables(debugLaunchEnvVars, env, { overwrite: true });
+    normalizeSearchPathEnvVar(env, pathVariableNames);
 
     // Append the PYTHONPATH and PATH variables.
-    envParser.appendPath(env, debugLaunchEnvVars[pathVariableName]);
+    const debugLaunchSearchPath = getSearchPathEnvVar(debugLaunchEnvVars, pathVariableNames);
+    if (debugLaunchSearchPath) {
+        envParser.appendPath(env, debugLaunchSearchPath);
+    }
     envParser.appendPythonPath(env, debugLaunchEnvVars.PYTHONPATH);
 
     if (typeof env[pathVariableName] === 'string' && env[pathVariableName]!.length > 0) {
         // Now merge this path with the current system path.
         // We need to do this to ensure the PATH variable always has the system PATHs as well.
-        envParser.appendPath(env, process.env[pathVariableName]!);
+        const processSearchPath = getSearchPathEnvVar(process.env, pathVariableNames);
+        if (processSearchPath) {
+            envParser.appendPath(env, processSearchPath);
+        }
     }
     if (typeof env.PYTHONPATH === 'string' && env.PYTHONPATH.length > 0) {
         // We didn't have a value for PATH earlier and now we do.
@@ -47,14 +87,17 @@ export async function getDebugEnvironmentVariables(args: LaunchRequestArguments)
         // As we're spawning the process, we need to ensure all env variables are passed.
         // Including those from the current process (i.e. everything, not just custom vars).
         envParser.mergeVariables(process.env, env);
+        normalizeSearchPathEnvVar(env, pathVariableNames);
 
-        if (env[pathVariableName] === undefined && typeof process.env[pathVariableName] === 'string') {
-            env[pathVariableName] = process.env[pathVariableName];
+        const processSearchPath = getSearchPathEnvVar(process.env, pathVariableNames);
+        if (env[pathVariableName] === undefined && typeof processSearchPath === 'string') {
+            env[pathVariableName] = processSearchPath;
         }
         if (env.PYTHONPATH === undefined && typeof process.env.PYTHONPATH === 'string') {
             env.PYTHONPATH = process.env.PYTHONPATH;
         }
     }
+    normalizeSearchPathEnvVar(env, pathVariableNames);
 
     if (!env.hasOwnProperty('PYTHONIOENCODING')) {
         env.PYTHONIOENCODING = 'UTF-8';
diff --git a/src/test/unittest/configuration/resolvers/helper.unit.test.ts b/src/test/unittest/configuration/resolvers/helper.unit.test.ts
index c2d6d483..e9125820 100644
--- a/src/test/unittest/configuration/resolvers/helper.unit.test.ts
+++ b/src/test/unittest/configuration/resolvers/helper.unit.test.ts
@@ -8,8 +8,13 @@ import * as sinon from 'sinon';
 import * as typemoq from 'typemoq';
 import { TextDocument, TextEditor } from 'vscode';
 import { PYTHON_LANGUAGE } from '../../../../extension/common/constants';
+import * as platform from '../../../../extension/common/platform';
 import * as vscodeapi from '../../../../extension/common/vscodeapi';
-import { getProgram } from '../../../../extension/debugger/configuration/resolvers/helper';
+import {
+    getDebugEnvironmentVariables,
+    getProgram,
+} from '../../../../extension/debugger/configuration/resolvers/helper';
+import { LaunchRequestArguments } from '../../../../extension/types';
 
 suite('Debugging - Helpers', () => {
     let getActiveTextEditorStub: sinon.SinonStub;
@@ -67,4 +72,42 @@ suite('Debugging - Helpers', () => {
 
         expect(program).to.be.equal(undefined, 'Not undefined');
     });
+
+    test('Debug environment should not include duplicate Windows search path keys', async () => {
+        sinon.stub(platform, 'getOSType').returns(platform.OSType.Windows);
+
+        const originalPath = process.env.Path;
+        const originalPATH = process.env.PATH;
+        process.env.Path = 'C:\\Windows\\System32';
+        process.env.PATH = 'C:\\Tools';
+
+        try {
+            const launchEnv = { ['PATH']: 'C:\\Project\\.venv\\Scripts' };
+            const env = await getDebugEnvironmentVariables({
+                name: 'Python Debug Test',
+                type: 'debugpy',
+                request: 'launch',
+                env: launchEnv,
+                console: 'internalConsole',
+            } as unknown as LaunchRequestArguments);
+
+            expect(env).to.have.property('Path');
+            expect(env).not.to.have.property('PATH');
+            expect(env.Path).to.contain('C:\\Project\\.venv\\Scripts');
+            expect(env.Path).to.contain('C:\\Tools');
+            expect(env.Path!.split(';').filter((item) => item === 'C:\\Project\\.venv\\Scripts')).to.have.lengthOf(1);
+            expect(env.Path!.split(';').filter((item) => item === 'C:\\Tools')).to.have.lengthOf(1);
+        } finally {
+            if (originalPath === undefined) {
+                delete process.env.Path;
+            } else {
+                process.env.Path = originalPath;
+            }
+            if (originalPATH === undefined) {
+                delete process.env.PATH;
+            } else {
+                process.env.PATH = originalPATH;
+            }
+        }
+    });
 });