diff --git a/src/rules/__tests__/valid-expect.test.ts b/src/rules/__tests__/valid-expect.test.ts
index 78f9cc964..10434a43b 100644
--- a/src/rules/__tests__/valid-expect.test.ts
+++ b/src/rules/__tests__/valid-expect.test.ts
@@ -74,6 +74,35 @@ ruleTester.run('valid-expect', rule, {
         return expect(functionReturningAPromise()).resolves.toEqual(1).then(() => expect(Promise.resolve(2)).resolves.toBe(1));
       });
     `,
+    dedent`
+      expect.extend({
+        toResolve(obj) {
+          return this.isNot
+            ? expect(obj).toBe(true)
+            : expect(obj).resolves.not.toThrow();
+        }
+      });
+    `,
+    dedent`
+      expect.extend({
+        toResolve(obj) {
+          return this.isNot
+            ? expect(obj).resolves.not.toThrow()
+            : expect(obj).toBe(true);
+        }
+      });
+    `,
+    dedent`
+      expect.extend({
+        toResolve(obj) {
+          return this.isNot
+            ? expect(obj).toBe(true)
+            : anotherCondition
+            ? expect(obj).resolves.not.toThrow()
+            : expect(obj).toBe(false)
+        }
+      });
+    `,
     {
       code: 'expect(1).toBe(2);',
       options: [{ maxArgs: 2 }],
@@ -369,6 +398,63 @@ ruleTester.run('valid-expect', rule, {
       ],
     },
 
+    {
+      code: dedent`
+        expect.extend({
+          toResolve(obj) {
+            this.isNot
+              ? expect(obj).toBe(true)
+              : expect(obj).resolves.not.toThrow();
+          }
+        });
+      `,
+      errors: [
+        {
+          column: 9,
+          endColumn: 43,
+          messageId: 'asyncMustBeAwaited',
+        },
+      ],
+    },
+    {
+      code: dedent`
+        expect.extend({
+          toResolve(obj) {
+            this.isNot
+              ? expect(obj).resolves.not.toThrow()
+              : expect(obj).toBe(true);
+          }
+        });
+      `,
+      errors: [
+        {
+          column: 9,
+          endColumn: 43,
+          messageId: 'asyncMustBeAwaited',
+        },
+      ],
+    },
+    {
+      code: dedent`
+        expect.extend({
+          toResolve(obj) {
+            this.isNot
+              ? expect(obj).toBe(true)
+              : anotherCondition
+              ? expect(obj).resolves.not.toThrow()
+              : expect(obj).toBe(false)
+          }
+        });
+      `,
+      errors: [
+        {
+          column: 9,
+          endColumn: 43,
+          messageId: 'asyncMustBeAwaited',
+        },
+      ],
+    },
+
     // expect().resolves
     {
       code:
diff --git a/src/rules/valid-expect.ts b/src/rules/valid-expect.ts
index 2869ecc64..f0118b987 100644
--- a/src/rules/valid-expect.ts
+++ b/src/rules/valid-expect.ts
@@ -80,14 +80,23 @@ const isAcceptableReturnNode = (
   node: TSESTree.Node,
   allowReturn: boolean,
 ): node is
+  | TSESTree.ConditionalExpression
   | TSESTree.ArrowFunctionExpression
   | TSESTree.AwaitExpression
-  | TSESTree.ReturnStatement =>
-  (allowReturn && node.type === AST_NODE_TYPES.ReturnStatement) ||
-  [
+  | TSESTree.ReturnStatement => {
+  if (allowReturn && node.type === AST_NODE_TYPES.ReturnStatement) {
+    return true;
+  }
+
+  if (node.type === AST_NODE_TYPES.ConditionalExpression && node.parent) {
+    return isAcceptableReturnNode(node.parent, allowReturn);
+  }
+
+  return [
     AST_NODE_TYPES.ArrowFunctionExpression,
     AST_NODE_TYPES.AwaitExpression,
   ].includes(node.type);
+};
 
 const isNoAssertionsParentNode = (node: TSESTree.Node): boolean =>
   node.type === AST_NODE_TYPES.ExpressionStatement ||