diff --git a/packages/insomnia-app/app/ui/components/editors/__tests__/environment-editor.test.ts b/packages/insomnia-app/app/ui/components/editors/__tests__/environment-editor.test.ts
index 0fe317ddcd..5b6997c153 100644
--- a/packages/insomnia-app/app/ui/components/editors/__tests__/environment-editor.test.ts
+++ b/packages/insomnia-app/app/ui/components/editors/__tests__/environment-editor.test.ts
@@ -1,26 +1,149 @@
 import { NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME } from '../../../../templating';
-import { ensureKeyIsValid } from '../environment-editor';
+import { checkNestedKeys, ensureKeyIsValid } from '../environment-editor';
 
-describe('ensureKeyIsValid', () => {
-  it.each(['$', '$a', '$ab'])('%s should be invalid when as key begins with $', key => {
-    expect(ensureKeyIsValid(key)).toBe(`"${key}" cannot begin with '$' or contain a '.'`);
+describe('ensureKeyIsValid()', () => {
+  it.each([
+    '$',
+    '$a',
+    '$ab',
+  ])('"%s" should be invalid when key begins with $', key => {
+    expect(ensureKeyIsValid(key, false)).toBe(`"${key}" cannot begin with '$' or contain a '.'`);
   });
 
-  it.each(['.', 'a.', '.a', 'a.b'])('%s should be invalid when key contains .', key => {
-    expect(ensureKeyIsValid(key)).toBe(`"${key}" cannot begin with '$' or contain a '.'`);
+  it.each([
+    '.',
+    'a.',
+    '.a',
+    'a.b',
+  ])('"%s" should be invalid when key contains .', key => {
+    expect(ensureKeyIsValid(key, false)).toBe(`"${key}" cannot begin with '$' or contain a '.'`);
   });
 
-  it.each(['$a.b', '$.'])('%s should be invalid when key starts with $ and contains .', key => {
-    expect(ensureKeyIsValid(key)).toBe(`"${key}" cannot begin with '$' or contain a '.'`);
+  it.each([
+    '$a.b',
+    '$.',
+  ])('"%s" should be invalid when key starts with $ and contains .', key => {
+    expect(ensureKeyIsValid(key, false)).toBe(`"${key}" cannot begin with '$' or contain a '.'`);
   });
 
-  const name = NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME;
-
-  it(`${name} as a key should be invalid`, () => {
-    expect(ensureKeyIsValid(name)).toBe(`"${name}" is a reserved key`);
+  it.each([
+    '_',
+  ])('"%s" should be invalid when key is _', key => {
+    expect(ensureKeyIsValid(key, true)).toBe(`"${key}" is a reserved key`);
   });
 
-  it.each(['a', 'ab', 'a$', 'a$b', 'a-b', `a${name}b`, `${name}ab`])('%s should be valid', key => {
-    expect(ensureKeyIsValid(key)).toBe(null);
+  it.each([
+    '_',
+    'a',
+    'ab',
+    'a$',
+    'a$b',
+    'a-b',
+    `a${NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME}b`,
+    `${NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME}ab`,
+  ])('"%s" should be valid as a nested key', key => {
+    expect(ensureKeyIsValid(key, false)).toBe(null);
+  });
+
+  it.each([
+    'a',
+    'ab',
+    'a$',
+    'a$b',
+    'a-b',
+    `a${NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME}b`,
+    `${NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME}ab`,
+  ])('"%s" should be valid as a root value', key => {
+    expect(ensureKeyIsValid(key, true)).toBe(null);
+  });
+});
+
+describe('checkNestedKeys()', () => {
+  it('should check root property and error', () => {
+    const obj = {
+      'base-url': 'https://api.insomnia.rest',
+      '$nes.ted': {
+        'path-with-hyphens': '/path-with-hyphen',
+      },
+      'ar-ray': [
+        '/first',
+        {
+          'second': 'second',
+        },
+        {
+          'third': 'third',
+        },
+      ],
+    };
+
+    const err = checkNestedKeys(obj);
+
+    expect(err).toBe('"$nes.ted" cannot begin with \'$\' or contain a \'.\'');
+  });
+
+  it('should check nested property and error', () => {
+    const obj = {
+      'base-url': 'https://api.insomnia.rest',
+      'nested': {
+        '$path-wi.th-hyphens': '/path-with-hyphen',
+      },
+      'ar-ray': [
+        '/first',
+        {
+          'second': 'second',
+        },
+        {
+          'third': 'third',
+        },
+      ],
+    };
+
+    const err = checkNestedKeys(obj);
+
+    expect(err).toBe('"$path-wi.th-hyphens" cannot begin with \'$\' or contain a \'.\'');
+  });
+
+  it('should check for complex objects inside array', () => {
+    const obj = {
+      'base-url': 'https://api.insomnia.rest',
+      'nested': {
+        'path-with-hyphens': '/path-with-hyphen',
+      },
+      'ar-ray': [
+        '/first',
+        {
+          'second': 'second',
+        },
+        {
+          'thi.rd': 'third',
+        },
+      ],
+    };
+
+    const err = checkNestedKeys(obj);
+
+    expect(err).toBe('"thi.rd" cannot begin with \'$\' or contain a \'.\'');
+  });
+
+  it('should check nested properties and pass', () => {
+    const obj = {
+      'base-url': 'https://api.insomnia.rest',
+      'nested': {
+        'path-with-hyphens': '/path-with-hyphen',
+      },
+      'ar-ray': [
+        '/first',
+        {
+          'second': 'second',
+        },
+        {
+          'third': 'third',
+        },
+      ],
+    };
+
+    const err = checkNestedKeys(obj);
+
+    expect(err).toBe(null);
   });
 });
diff --git a/packages/insomnia-app/app/ui/components/editors/environment-editor.tsx b/packages/insomnia-app/app/ui/components/editors/environment-editor.tsx
index b7add5446d..fbded178ff 100644
--- a/packages/insomnia-app/app/ui/components/editors/environment-editor.tsx
+++ b/packages/insomnia-app/app/ui/components/editors/environment-editor.tsx
@@ -5,21 +5,52 @@ import React, { PureComponent } from 'react';
 import { AUTOBIND_CFG, JSON_ORDER_PREFIX, JSON_ORDER_SEPARATOR } from '../../../common/constants';
 import { NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME } from '../../../templating';
 import CodeEditor from '../codemirror/code-editor';
+
 // NeDB field names cannot begin with '$' or contain a period '.'
 // Docs: https://github.com/DeNA/nedb#inserting-documents
 const INVALID_NEDB_KEY_REGEX = /^\$|\./;
-export const ensureKeyIsValid = (key: string): string | null => {
+
+export const ensureKeyIsValid = (key: string, isRoot: boolean): string | null => {
   if (key.match(INVALID_NEDB_KEY_REGEX)) {
     return `"${key}" cannot begin with '$' or contain a '.'`;
   }
 
-  if (key === NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME) {
-    return `"${NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME}" is a reserved key`; // verbiage WIP
+  if (key === NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME && isRoot) {
+    return `"${NUNJUCKS_TEMPLATE_GLOBAL_PROPERTY_NAME}" is a reserved key`;
   }
 
   return null;
 };
 
+/**
+ * Recursively check nested keys in and immediately return when an invalid key found
+ */
+export function checkNestedKeys(obj: Record<string, any>, isRoot = true): string | null {
+  for (const key in obj) {
+    let result: string | null = null;
+
+    // Check current key
+    result = ensureKeyIsValid(key, isRoot);
+
+    // Exit if necessary
+    if (result) {
+      return result;
+    }
+
+    // Check nested keys
+    if (typeof obj[key] === 'object') {
+      result = checkNestedKeys(obj[key], false);
+    }
+
+    // Exit if necessary
+    if (result) {
+      return result;
+    }
+  }
+
+  return null;
+}
+
 export interface EnvironmentInfo {
   object: Record<string, any>;
   propertyOrder: Record<string, any> | null;
@@ -64,14 +95,11 @@ class EnvironmentEditor extends PureComponent<Props, State> {
     }
 
     // Check for invalid key names
-    // TODO: these only check root properties, not nested properties
     if (value && value.object) {
-      for (const key of Object.keys(value.object)) {
-        error = ensureKeyIsValid(key);
-
-        if (error) {
-          break;
-        }
+      // Check root and nested properties
+      const err = checkNestedKeys(value.object);
+      if (err) {
+        error = err;
       }
     }