diff --git a/rules/no-nested-ternary.js b/rules/no-nested-ternary.js
index 6780b4cef5..b73d44c936 100644
--- a/rules/no-nested-ternary.js
+++ b/rules/no-nested-ternary.js
@@ -2,41 +2,33 @@
 const {isParenthesized} = require('eslint-utils');
 const getDocumentationUrl = require('./utils/get-documentation-url');
 
-const MESSAGE_ID = 'no-nested-ternary';
+const MESSAGE_ID_TOO_DEEP = 'too-deep';
+const MESSAGE_ID_SHOULD_PARENTHESIZED = 'should-parenthesized';
 const messages = {
-	[MESSAGE_ID]: 'Do not nest ternary expressions.'
+	[MESSAGE_ID_TOO_DEEP]: 'Do not nest ternary expressions.',
+	[MESSAGE_ID_SHOULD_PARENTHESIZED]: 'Nest ternary expression should be parenthesized.'
 };
 
+const nestTernarySelector = level => `:not(ConditionalExpression)${' > ConditionalExpression'.repeat(level)}`;
+
 const create = context => {
 	const sourceCode = context.getSourceCode();
 
 	return {
-		ConditionalExpression: node => {
-			const nodesToCheck = [node.alternate, node.consequent];
-
-			for (const childNode of nodesToCheck) {
-				if (childNode.type !== 'ConditionalExpression') {
-					continue;
-				}
-
-				// Nesting more than one level not allowed.
-				if (
-					childNode.alternate.type === 'ConditionalExpression' ||
-					childNode.consequent.type === 'ConditionalExpression'
-				) {
-					// TODO: Improve report location
-					context.report({node, messageId: MESSAGE_ID});
-					break;
-				} else if (!isParenthesized(childNode, sourceCode)) {
-					context.report({
-						node: childNode,
-						messageId: MESSAGE_ID,
-						fix: fixer => [
-							fixer.insertTextBefore(childNode, '('),
-							fixer.insertTextAfter(childNode, ')')
-						]
-					});
-				}
+		[nestTernarySelector(3)]: node => {
+			// Nesting more than one level not allowed.
+			context.report({node, messageId: MESSAGE_ID_TOO_DEEP});
+		},
+		[nestTernarySelector(2)]: node => {
+			if (!isParenthesized(node, sourceCode)) {
+				context.report({
+					node,
+					messageId: MESSAGE_ID_SHOULD_PARENTHESIZED,
+					fix: fixer => [
+						fixer.insertTextBefore(node, '('),
+						fixer.insertTextAfter(node, ')')
+					]
+				});
 			}
 		}
 	};
diff --git a/test/no-nested-ternary.js b/test/no-nested-ternary.js
index 6c913e1dea..47e005ac3e 100644
--- a/test/no-nested-ternary.js
+++ b/test/no-nested-ternary.js
@@ -14,12 +14,6 @@ const typescriptRuleTester = avaRuleTester(test, {
 	parser: require.resolve('@typescript-eslint/parser')
 });
 
-const errors = [
-	{
-		messageId: 'no-nested-ternary'
-	}
-];
-
 ruleTester.run('no-nested-ternary', rule, {
 	valid: [
 		'const foo = i > 5 ? true : false;',
@@ -33,43 +27,36 @@ ruleTester.run('no-nested-ternary', rule, {
 	invalid: [
 		{
 			code: 'const foo = i > 5 ? true : (i < 100 ? true : (i < 1000 ? true : false));',
-			errors
+			errors: 1
 		},
 		{
 			code: 'const foo = i > 5 ? true : (i < 100 ? (i > 50 ? false : true) : false);',
-			errors
+			errors: 1
 		},
 		{
 			code: 'const foo = i > 5 ? i < 100 ? true : false : true;',
 			output: 'const foo = i > 5 ? (i < 100 ? true : false) : true;',
-			errors
+			errors: 1
 		},
 		{
 			code: 'const foo = i > 5 ? i < 100 ? true : false : i < 100 ? true : false;',
 			output: 'const foo = i > 5 ? (i < 100 ? true : false) : (i < 100 ? true : false);',
-			errors: [
-				{
-					column: 21
-				},
-				{
-					column: 46
-				}
-			]
+			errors: 2
 		},
 		{
 			code: 'const foo = i > 5 ? true : i < 100 ? true : false;',
 			output: 'const foo = i > 5 ? true : (i < 100 ? true : false);',
-			errors
+			errors: 1
 		},
 		{
 			code: 'foo ? bar : baz === qux ? quxx : foobar;',
 			output: 'foo ? bar : (baz === qux ? quxx : foobar);',
-			errors
+			errors: 1
 		},
 		{
 			code: 'foo ? baz === qux ? quxx : foobar : bar;',
 			output: 'foo ? (baz === qux ? quxx : foobar) : bar;',
-			errors
+			errors: 1
 		}
 	]
 });
@@ -96,5 +83,19 @@ const visualizeTester = visualizeRuleTester(test, {
 	}
 });
 visualizeTester.run('no-nested-ternary', rule, [
-	'const foo = i > 5 ? true : (i < 100 ? true : (i < 1000 ? true : false));'
+	'const foo = i > 5 ? i < 100 ? true : false : i < 100 ? true : false;',
+	'const foo = i > 5 ? true : (i < 100 ? true : (i < 1000 ? true : false));',
+	outdent`
+		const foo = a ?
+			b :
+			(
+				c ?
+					d :
+					(
+						e ?
+							f :
+							(g ? h : i)
+					)
+			)
+	`
 ]);
diff --git a/test/snapshots/no-nested-ternary.js.md b/test/snapshots/no-nested-ternary.js.md
index ab56544d29..feb015d7b6 100644
--- a/test/snapshots/no-nested-ternary.js.md
+++ b/test/snapshots/no-nested-ternary.js.md
@@ -6,6 +6,25 @@ Generated by [AVA](https://avajs.dev).
 
 ## no-nested-ternary - #1
 
+> Snapshot 1
+
+    `␊
+    Input:␊
+      1 | const foo = i > 5 ? i < 100 ? true : false : i < 100 ? true : false;␊
+    ␊
+    Output:␊
+      1 | const foo = i > 5 ? (i < 100 ? true : false) : (i < 100 ? true : false);␊
+    ␊
+    Error 1/2:␊
+    > 1 | const foo = i > 5 ? i < 100 ? true : false : i < 100 ? true : false;␊
+        |                     ^^^^^^^^^^^^^^^^^^^^^^ Nest ternary expression should be parenthesized.␊
+    Error 2/2:␊
+    > 1 | const foo = i > 5 ? i < 100 ? true : false : i < 100 ? true : false;␊
+        |                                              ^^^^^^^^^^^^^^^^^^^^^^ Nest ternary expression should be parenthesized.␊
+    `
+
+## no-nested-ternary - #2
+
 > Snapshot 1
 
     `␊
@@ -17,5 +36,43 @@ Generated by [AVA](https://avajs.dev).
     ␊
     Error 1/1:␊
     > 1 | const foo = i > 5 ? true : (i < 100 ? true : (i < 1000 ? true : false));␊
-        |             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Do not nest ternary expressions.␊
+        |                                               ^^^^^^^^^^^^^^^^^^^^^^^ Do not nest ternary expressions.␊
+    `
+
+## no-nested-ternary - #3
+
+> Snapshot 1
+
+    `␊
+    Input:␊
+       1 | const foo = a ?␊
+       2 | 	b :␊
+       3 | 	(␊
+       4 | 		c ?␊
+       5 | 			d :␊
+       6 | 			(␊
+       7 | 				e ?␊
+       8 | 					f :␊
+       9 | 					(g ? h : i)␊
+      10 | 			)␊
+      11 | 	)␊
+    ␊
+    Output:␊
+    [Same as input]␊
+    ␊
+    Error 1/1:␊
+       1 | const foo = a ?␊
+       2 | 	b :␊
+       3 | 	(␊
+       4 | 		c ?␊
+       5 | 			d :␊
+       6 | 			(␊
+    >  7 | 				e ?␊
+         | 				^^^␊
+    >  8 | 					f :␊
+         | ^^^^^^^^␊
+    >  9 | 					(g ? h : i)␊
+         | ^^^^^^^^^^^^^^^^^ Do not nest ternary expressions.␊
+      10 | 			)␊
+      11 | 	)␊
     `
diff --git a/test/snapshots/no-nested-ternary.js.snap b/test/snapshots/no-nested-ternary.js.snap
index 438a2ecc69..b4d43fa14b 100644
Binary files a/test/snapshots/no-nested-ternary.js.snap and b/test/snapshots/no-nested-ternary.js.snap differ