diff --git a/tests/ui/if_not_else.fixed b/tests/ui/if_not_else.fixed
index 6c646b0b963d..11d1e13179c4 100644
--- a/tests/ui/if_not_else.fixed
+++ b/tests/ui/if_not_else.fixed
@@ -28,4 +28,46 @@ fn main() {
     } else {
         println!("Bunny");
     }
+
+    if (foo() && bla()) {
+        println!("both true");
+    } else {
+        #[cfg(not(debug_assertions))]
+        println!("not debug");
+        #[cfg(debug_assertions)]
+        println!("debug");
+        if foo() {
+            println!("foo");
+        } else if bla() {
+            println!("bla");
+        } else {
+            println!("both false");
+        }
+    }
+}
+
+fn with_comments() {
+    if foo() {
+        println!("foo"); /* foo */
+    } else {
+        /* foo is false */
+        println!("foo is false");
+    }
+
+    if bla() {
+        println!("bla"); // bla
+    } else {
+        // bla is false
+        println!("bla");
+    }
+}
+
+fn with_annotations() {
+    #[cfg(debug_assertions)]
+    if foo() {
+        println!("foo"); /* foo */
+    } else {
+        /* foo is false */
+        println!("foo is false");
+    }
 }
diff --git a/tests/ui/if_not_else.rs b/tests/ui/if_not_else.rs
index fd30e3702a27..fcc67e163e8a 100644
--- a/tests/ui/if_not_else.rs
+++ b/tests/ui/if_not_else.rs
@@ -28,4 +28,46 @@ fn main() {
     } else {
         println!("Bunny");
     }
+
+    if !(foo() && bla()) {
+        #[cfg(not(debug_assertions))]
+        println!("not debug");
+        #[cfg(debug_assertions)]
+        println!("debug");
+        if foo() {
+            println!("foo");
+        } else if bla() {
+            println!("bla");
+        } else {
+            println!("both false");
+        }
+    } else {
+        println!("both true");
+    }
+}
+
+fn with_comments() {
+    if !foo() {
+        /* foo is false */
+        println!("foo is false");
+    } else {
+        println!("foo"); /* foo */
+    }
+
+    if !bla() {
+        // bla is false
+        println!("bla");
+    } else {
+        println!("bla"); // bla
+    }
+}
+
+fn with_annotations() {
+    #[cfg(debug_assertions)]
+    if !foo() {
+        /* foo is false */
+        println!("foo is false");
+    } else {
+        println!("foo"); /* foo */
+    }
 }
diff --git a/tests/ui/if_not_else.stderr b/tests/ui/if_not_else.stderr
index 01d6767004d9..b01cb5af11f7 100644
--- a/tests/ui/if_not_else.stderr
+++ b/tests/ui/if_not_else.stderr
@@ -42,5 +42,99 @@ LL +         println!("Bugs");
 LL +     }
    |
 
-error: aborting due to 2 previous errors
+error: unnecessary boolean `not` operation
+  --> tests/ui/if_not_else.rs:32:5
+   |
+LL | /     if !(foo() && bla()) {
+LL | |         #[cfg(not(debug_assertions))]
+LL | |         println!("not debug");
+LL | |         #[cfg(debug_assertions)]
+...  |
+LL | |         println!("both true");
+LL | |     }
+   | |_____^
+   |
+help: try
+   |
+LL ~     if (foo() && bla()) {
+LL +         println!("both true");
+LL +     } else {
+LL +         #[cfg(not(debug_assertions))]
+LL +         println!("not debug");
+LL +         #[cfg(debug_assertions)]
+LL +         println!("debug");
+LL +         if foo() {
+LL +             println!("foo");
+LL +         } else if bla() {
+LL +             println!("bla");
+LL +         } else {
+LL +             println!("both false");
+LL +         }
+LL +     }
+   |
+
+error: unnecessary boolean `not` operation
+  --> tests/ui/if_not_else.rs:50:5
+   |
+LL | /     if !foo() {
+LL | |         /* foo is false */
+LL | |         println!("foo is false");
+LL | |     } else {
+LL | |         println!("foo"); /* foo */
+LL | |     }
+   | |_____^
+   |
+help: try
+   |
+LL ~     if foo() {
+LL +         println!("foo"); /* foo */
+LL +     } else {
+LL +         /* foo is false */
+LL +         println!("foo is false");
+LL +     }
+   |
+
+error: unnecessary boolean `not` operation
+  --> tests/ui/if_not_else.rs:57:5
+   |
+LL | /     if !bla() {
+LL | |         // bla is false
+LL | |         println!("bla");
+LL | |     } else {
+LL | |         println!("bla"); // bla
+LL | |     }
+   | |_____^
+   |
+help: try
+   |
+LL ~     if bla() {
+LL +         println!("bla"); // bla
+LL +     } else {
+LL +         // bla is false
+LL +         println!("bla");
+LL +     }
+   |
+
+error: unnecessary boolean `not` operation
+  --> tests/ui/if_not_else.rs:67:5
+   |
+LL | /     if !foo() {
+LL | |         /* foo is false */
+LL | |         println!("foo is false");
+LL | |     } else {
+LL | |         println!("foo"); /* foo */
+LL | |     }
+   | |_____^
+   |
+help: try
+   |
+LL ~     if foo() {
+LL +         println!("foo"); /* foo */
+LL +     } else {
+LL +         /* foo is false */
+LL +         println!("foo is false");
+LL +     }
+   |
+
+error: aborting due to 6 previous errors