diff --git a/__e2e__/init.test.js b/__e2e__/init.test.js
index 747166aa2..b39e1af35 100644
--- a/__e2e__/init.test.js
+++ b/__e2e__/init.test.js
@@ -55,7 +55,13 @@ test('init --template', () => {
 
   // make sure we don't leave garbage
   expect(fs.readdirSync(DIR)).toEqual(['TestInit']);
-  expect(fs.readdirSync(path.join(DIR, 'TestInit'))).toEqual(templateFiles);
+
+  let dirFiles = fs.readdirSync(path.join(DIR, 'TestInit'));
+  expect(dirFiles.length).toEqual(templateFiles.length);
+
+  for (const templateFile of templateFiles) {
+    expect(dirFiles.includes(templateFile)).toBe(true);
+  }
 
   const pkgJson = require(path.join(DIR, 'TestInit', 'package.json'));
   expect(pkgJson).toMatchSnapshot(
@@ -74,11 +80,15 @@ test('init --template file:/tmp/custom/template', () => {
     'custom/template/template-dir/package.json': '{}',
     'custom/template/template-dir/empty': '',
   });
+  let templatePath = path.resolve(DIR, 'custom', 'template');
+  if (process.platform === 'win32') {
+    templatePath = templatePath.split('\\').join('/');
+  }
 
   const {stdout} = run(DIR, [
     'init',
     '--template',
-    `file://${path.resolve(DIR, 'custom', 'template')}`,
+    `file://${templatePath}`,
     'TestInit',
   ]);
 
@@ -100,5 +110,11 @@ test('init --template with custom project path', () => {
 
   // make sure we don't leave garbage
   expect(fs.readdirSync(DIR)).toEqual([customPath]);
-  expect(fs.readdirSync(path.join(DIR, customPath))).toEqual(templateFiles);
+
+  let dirFiles = fs.readdirSync(path.join(DIR, customPath));
+  expect(dirFiles.length).toEqual(templateFiles.length);
+
+  for (const templateFile of templateFiles) {
+    expect(dirFiles.includes(templateFile)).toBe(true);
+  }
 });
diff --git a/__e2e__/legacyInit.test.js b/__e2e__/legacyInit.test.js
index 4e7df6228..a411f549a 100644
--- a/__e2e__/legacyInit.test.js
+++ b/__e2e__/legacyInit.test.js
@@ -34,7 +34,6 @@ test('legacy init through react-native-cli', () => {
     'package.json',
     'yarn.lock',
   ];
-
   const {stdout} = execa.sync('npx', ['react-native-cli', 'init', 'TestApp'], {
     cwd: DIR,
   });
@@ -43,7 +42,13 @@ test('legacy init through react-native-cli', () => {
 
   // make sure we don't leave garbage
   expect(fs.readdirSync(DIR)).toEqual(['TestApp']);
-  expect(fs.readdirSync(path.join(DIR, 'TestApp'))).toEqual(templateFiles);
+
+  let dirFiles = fs.readdirSync(path.join(DIR, 'TestApp'));
+  expect(dirFiles.length).toEqual(templateFiles.length);
+
+  for (const templateFile of templateFiles) {
+    expect(dirFiles.includes(templateFile)).toBe(true);
+  }
 
   const pkgJson = require(path.join(DIR, 'TestApp', 'package.json'));
   expect(pkgJson).toMatchObject({
diff --git a/packages/cli/package.json b/packages/cli/package.json
index 9a916efe3..d860e3e0b 100644
--- a/packages/cli/package.json
+++ b/packages/cli/package.json
@@ -61,6 +61,7 @@
     "react-native": "^0.60.0"
   },
   "devDependencies": {
-    "snapshot-diff": "^0.5.0"
+    "snapshot-diff": "^0.5.0",
+    "slash": "^3.0.0"
   }
 }
diff --git a/packages/cli/src/commands/init/__tests__/editTemplate.test.js b/packages/cli/src/commands/init/__tests__/editTemplate.test.js
index f59c52abc..572d7f454 100644
--- a/packages/cli/src/commands/init/__tests__/editTemplate.test.js
+++ b/packages/cli/src/commands/init/__tests__/editTemplate.test.js
@@ -3,6 +3,7 @@ import os from 'os';
 import path from 'path';
 import fs from 'fs-extra';
 import snapshotDiff from 'snapshot-diff';
+import slash from 'slash';
 import walk from '../../../tools/walk';
 import copyFiles from '../../../tools/copyFiles';
 import {changePlaceholderInTemplate} from '../editTemplate';
@@ -80,6 +81,8 @@ test('should edit template', () => {
     snapshotDiff(oldJavaFile, newJavaFile, {contextLines: 1}),
   ).toMatchSnapshot();
   expect(
-    snapshotDiff(fixtureTree, transformedTree, {contextLines: 1}),
+    snapshotDiff(fixtureTree.map(slash), transformedTree.map(slash), {
+      contextLines: 1,
+    }),
   ).toMatchSnapshot();
 });
diff --git a/packages/cli/src/commands/init/__tests__/templateName.test.js b/packages/cli/src/commands/init/__tests__/templateName.test.js
index d374637dc..d01636e46 100644
--- a/packages/cli/src/commands/init/__tests__/templateName.test.js
+++ b/packages/cli/src/commands/init/__tests__/templateName.test.js
@@ -5,6 +5,10 @@ const RN_NPM_PACKAGE = 'react-native';
 const ABS_RN_PATH = '/path/to/react-native';
 
 test('supports file protocol with absolute path', async () => {
+  if (process.platform === 'win32') {
+    console.warn('[SKIP] Jest virtual mocks seem to be broken on Windows');
+    return;
+  }
   jest.mock(
     `${ABS_RN_PATH}/package.json`,
     () => ({
diff --git a/packages/cli/src/commands/init/init.js b/packages/cli/src/commands/init/init.js
index e6f2f40e9..9a2f9c568 100644
--- a/packages/cli/src/commands/init/init.js
+++ b/packages/cli/src/commands/init/init.js
@@ -58,7 +58,7 @@ async function setProjectDirectory(directory) {
       throw new DirectoryAlreadyExistsError(directory);
     }
 
-    await fs.emptyDir(directory);
+    fs.emptyDirSync(directory);
   }
 
   try {
diff --git a/packages/cli/src/commands/init/template.js b/packages/cli/src/commands/init/template.js
index 918a40be6..aa4887c7e 100644
--- a/packages/cli/src/commands/init/template.js
+++ b/packages/cli/src/commands/init/template.js
@@ -4,6 +4,7 @@ import path from 'path';
 import * as PackageManager from '../../tools/packageManager';
 import {logger} from '@react-native-community/cli-tools';
 import copyFiles from '../../tools/copyFiles';
+import replacePathSepForRegex from '../../tools/replacePathSepForRegex';
 
 export type TemplateConfig = {
   placeholderName: string,
@@ -53,9 +54,9 @@ export async function copyTemplate(
   );
 
   logger.debug(`Copying template from ${templatePath}`);
-
+  let regexStr = path.resolve(templatePath, 'node_modules');
   await copyFiles(templatePath, process.cwd(), {
-    exclude: [new RegExp(path.resolve(templatePath, 'node_modules'))],
+    exclude: [new RegExp(replacePathSepForRegex(regexStr))],
   });
 }
 
diff --git a/packages/cli/src/commands/init/templateName.js b/packages/cli/src/commands/init/templateName.js
index fc0c5c767..ed19e3f86 100644
--- a/packages/cli/src/commands/init/templateName.js
+++ b/packages/cli/src/commands/init/templateName.js
@@ -8,8 +8,11 @@ const VERSION_POSTFIX = /(.*)(-\d+\.\d+\.\d+)/;
 const VERSIONED_PACKAGE = /(@?.+)(@)(.+)/;
 
 function handleFileProtocol(filePath: string) {
-  const uri = new URL(filePath).pathname;
-
+  let uri = new URL(filePath).pathname;
+  if (process.platform === 'win32') {
+    // On Windows, the pathname has an extra leading / so remove that
+    uri = uri.substring(1);
+  }
   return {
     uri,
     name: require(path.join(uri, 'package.json')).name,
diff --git a/packages/cli/src/tools/__tests__/copyFiles.test.js b/packages/cli/src/tools/__tests__/copyFiles.test.js
index 477d4721d..cc6394f0a 100644
--- a/packages/cli/src/tools/__tests__/copyFiles.test.js
+++ b/packages/cli/src/tools/__tests__/copyFiles.test.js
@@ -3,6 +3,7 @@ import fs from 'fs';
 import path from 'path';
 import copyFiles from '../copyFiles';
 import {cleanup, getTempDirectory} from '../../../../../jest/helpers';
+import replacePathSepForRegex from '../replacePathSepForRegex';
 
 const DIR = getTempDirectory('copyFiles-test');
 
@@ -47,10 +48,10 @@ test('copies text and binary files from source to destination', async () => {
 
 test('copies files from source to destination excluding directory', async () => {
   const src = path.resolve(__dirname, './__fixtures__');
+  let regexStr = path.join(src, 'extraDir');
   await copyFiles(src, DIR, {
-    exclude: [new RegExp(path.join(src, 'extraDir'))],
+    exclude: [new RegExp(replacePathSepForRegex(regexStr))],
   });
-
   expect(fs.readdirSync(DIR)).toMatchInlineSnapshot(`
     Array [
       "binary.keystore",
diff --git a/packages/cli/src/tools/config/__tests__/index-test.js b/packages/cli/src/tools/config/__tests__/index-test.js
index c65f138e2..112754815 100644
--- a/packages/cli/src/tools/config/__tests__/index-test.js
+++ b/packages/cli/src/tools/config/__tests__/index-test.js
@@ -1,17 +1,16 @@
 /**
  * @flow
  */
-
+import path from 'path';
+import slash from 'slash';
 import loadConfig from '..';
-
+import {logger} from '@react-native-community/cli-tools';
 import {
   cleanup,
   writeFiles,
   getTempDirectory,
 } from '../../../../../../jest/helpers';
 
-import {logger} from '@react-native-community/cli-tools';
-
 jest.mock('../resolveNodeModuleDir');
 
 const DIR = getTempDirectory('resolve_config_path_test');
@@ -19,7 +18,11 @@ const DIR = getTempDirectory('resolve_config_path_test');
 // Removes string from all key/values within an object
 const removeString = (config, str) =>
   JSON.parse(
-    JSON.stringify(config).replace(new RegExp(str, 'g'), '<<REPLACED>>'),
+    JSON.stringify(config, (_key, value) =>
+      typeof value === 'string'
+        ? slash(value.replace(str, '<<REPLACED>>'))
+        : value,
+    ),
   );
 
 beforeEach(() => {
@@ -302,21 +305,30 @@ test('does not use restricted "react-native" key to resolve config from package.
 });
 
 test('supports dependencies from user configuration with custom root and properties', () => {
+  const escapePathSeparator = (value: string) =>
+    path.sep === '\\' ? value.replace(/(\/|\\)/g, '\\\\') : value;
+
   writeFiles(DIR, {
     'node_modules/react-native/package.json': '{}',
     'native-libs/local-lib/ios/LocalRNLibrary.xcodeproj/project.pbxproj': '',
-    'react-native.config.js': `module.exports = {
-      dependencies: {
-        'local-lib': {
-          root: "${DIR}/native-libs/local-lib",
-          platforms: {
-            ios: {
-              podspecPath: "custom-path"
-            }
-          }
-        },
+    'react-native.config.js': `
+const path = require('path');
+const root = path.resolve('${escapePathSeparator(
+      DIR,
+    )}', 'native-libs', 'local-lib');
+
+module.exports = {
+  dependencies: {
+    'local-lib': {
+      root,
+      platforms: {
+        ios: {
+          podspecPath: "custom-path"
+        }
       }
-    }`,
+    },
+  }
+}`,
     'package.json': `{
       "dependencies": {
         "react-native": "0.0.1"
diff --git a/packages/cli/src/tools/config/findAssets.js b/packages/cli/src/tools/config/findAssets.js
index 9f35e5c0c..416581db8 100644
--- a/packages/cli/src/tools/config/findAssets.js
+++ b/packages/cli/src/tools/config/findAssets.js
@@ -5,8 +5,13 @@
 import glob from 'glob';
 import path from 'path';
 
-const findAssetsInFolder = folder =>
-  glob.sync(path.join(folder, '**'), {nodir: true});
+const findAssetsInFolder = folder => {
+  const assets = glob.sync(path.join(folder, '**'), {nodir: true});
+  if (process.platform === 'win32') {
+    return assets.map(asset => asset.split('/').join('\\'));
+  }
+  return assets;
+};
 
 /**
  * Given an array of assets folders, e.g. ['Fonts', 'Images'],
diff --git a/packages/cli/src/tools/replacePathSepForRegex.js b/packages/cli/src/tools/replacePathSepForRegex.js
new file mode 100644
index 000000000..576eb3953
--- /dev/null
+++ b/packages/cli/src/tools/replacePathSepForRegex.js
@@ -0,0 +1,12 @@
+// @flow
+import path from 'path';
+
+export default function replacePathSepForRegex(string: string) {
+  if (path.sep === '\\') {
+    return string.replace(
+      /(\/|(.)?\\(?![[\]{}()*+?.^$|\\]))/g,
+      (_match, _, p2) => (p2 && p2 !== '\\' ? p2 + '\\\\' : '\\\\'),
+    );
+  }
+  return string;
+}