diff --git a/src/Psalm/Internal/Type/SimpleNegatedAssertionReconciler.php b/src/Psalm/Internal/Type/SimpleNegatedAssertionReconciler.php
index 42152b724..0d2ff8f01 100644
--- a/src/Psalm/Internal/Type/SimpleNegatedAssertionReconciler.php
+++ b/src/Psalm/Internal/Type/SimpleNegatedAssertionReconciler.php
@@ -586,6 +586,12 @@ class SimpleNegatedAssertionReconciler extends Reconciler
                 }
             }
 
+            if ($existing_var_type->hasBool()) {
+                $existing_var_type->removeType('bool');
+
+                $existing_var_type->addType(new Type\Atomic\TTrue);
+            }
+
             self::removeFalsyNegatedLiteralTypes(
                 $existing_var_type,
                 $did_remove_type
diff --git a/tests/AssertAnnotationTest.php b/tests/AssertAnnotationTest.php
index a5055c3ad..e35516475 100644
--- a/tests/AssertAnnotationTest.php
+++ b/tests/AssertAnnotationTest.php
@@ -1674,6 +1674,20 @@ class AssertAnnotationTest extends TestCase
                     }',
                 'error_message' => 'InvalidDocblock',
             ],
+            'assertNotEmptyOnBool' => [
+                '<?php
+                    /**
+                     * @param mixed $value
+                     * @psalm-assert !empty $value
+                     */
+                    function assertNotEmpty($value) : void {}
+
+                    function foo(bool $bar) : void {
+                        assertNotEmpty($bar);
+                        if ($bar) {}
+                    }',
+                'error_message' => 'RedundantConditionGivenDocblockType',
+            ],
         ];
     }
 }
diff --git a/tests/TypeReconciliation/ReconcilerTest.php b/tests/TypeReconciliation/ReconcilerTest.php
index 6e6fafc8d..935200d98 100644
--- a/tests/TypeReconciliation/ReconcilerTest.php
+++ b/tests/TypeReconciliation/ReconcilerTest.php
@@ -132,6 +132,7 @@ class ReconcilerTest extends \Psalm\Tests\TestCase
             'iterableWithParamsToTraversableWithParams' => ['Traversable<int, string>', '!array', 'iterable<int, string>'],
             'iterableAndObject' => ['Traversable<int, string>', 'object', 'iterable<int, string>'],
             'iterableAndNotObject' => ['array<int, string>', '!object', 'iterable<int, string>'],
+            'boolNotEmptyIsTrue' => ['true', '!empty', 'bool'],
         ];
     }