diff --git a/src/Psalm/Internal/Analyzer/Statements/Expression/EmptyAnalyzer.php b/src/Psalm/Internal/Analyzer/Statements/Expression/EmptyAnalyzer.php
index 3b9014f85..40bf489ea 100644
--- a/src/Psalm/Internal/Analyzer/Statements/Expression/EmptyAnalyzer.php
+++ b/src/Psalm/Internal/Analyzer/Statements/Expression/EmptyAnalyzer.php
@@ -8,8 +8,15 @@ use Psalm\Context;
 use Psalm\Internal\Analyzer\StatementsAnalyzer;
 use Psalm\Issue\ForbiddenCode;
 use Psalm\Issue\InvalidArgument;
+use Psalm\Issue\TypeDoesNotContainType;
 use Psalm\IssueBuffer;
 use Psalm\Type;
+use Psalm\Type\Atomic\TBool;
+use Psalm\Type\Atomic\TFalse;
+use Psalm\Type\Atomic\TTrue;
+use Psalm\Type\Union;
+
+use function count;
 
 /**
  * @internal
@@ -35,21 +42,68 @@ final class EmptyAnalyzer
             );
         }
 
-        if (($stmt_expr_type = $statements_analyzer->node_data->getType($stmt->expr))
-            && $stmt_expr_type->hasBool()
-            && $stmt_expr_type->isSingle()
-            && !$stmt_expr_type->from_docblock
-        ) {
-            IssueBuffer::maybeAdd(
-                new InvalidArgument(
-                    'Calling empty on a boolean value is almost certainly unintended',
-                    new CodeLocation($statements_analyzer->getSource(), $stmt->expr),
-                    'empty',
-                ),
-                $statements_analyzer->getSuppressedIssues(),
-            );
+        $expr_type = $statements_analyzer->node_data->getType($stmt->expr);
+
+        if ($expr_type) {
+            if ($expr_type->hasBool()
+                && $expr_type->isSingle()
+                && !$expr_type->from_docblock
+            ) {
+                IssueBuffer::maybeAdd(
+                    new InvalidArgument(
+                        'Calling empty on a boolean value is almost certainly unintended',
+                        new CodeLocation($statements_analyzer->getSource(), $stmt->expr),
+                        'empty',
+                    ),
+                    $statements_analyzer->getSuppressedIssues(),
+                );
+            }
+
+            if ($expr_type->isAlwaysTruthy() && $expr_type->possibly_undefined === false) {
+                $stmt_type = new TFalse($expr_type->from_docblock);
+            } elseif ($expr_type->isAlwaysFalsy()) {
+                $stmt_type = new TTrue($expr_type->from_docblock);
+            } else {
+                $has_both = false;
+                $both_types = $expr_type->getBuilder();
+                if (count($expr_type->getAtomicTypes()) > 1) {
+                    foreach ($both_types->getAtomicTypes() as $key => $atomic_type) {
+                        if ($atomic_type->isTruthy()
+                            || $atomic_type->isFalsy()
+                            || $atomic_type instanceof TBool) {
+                            $both_types->removeType($key);
+                            continue;
+                        }
+
+                        $has_both = true;
+                    }
+                }
+
+                if ($has_both) {
+                    $both_types = $both_types->freeze();
+                    IssueBuffer::maybeAdd(
+                        new TypeDoesNotContainType(
+                            'Operand of type ' . $expr_type->getId() . ' contains ' .
+                            'type' . (count($both_types->getAtomicTypes()) > 1 ? 's' : '') . ' ' .
+                            $both_types->getId() . ', which can be falsy and truthy. ' .
+                            'This can cause possibly unexpected behavior. Use strict comparison instead.',
+                            new CodeLocation($statements_analyzer, $stmt),
+                            $expr_type->getId() . ' truthy-falsy',
+                        ),
+                        $statements_analyzer->getSuppressedIssues(),
+                    );
+                }
+
+                $stmt_type = new TBool();
+            }
+
+            $stmt_type = new Union([$stmt_type], [
+                'parent_nodes' => $expr_type->parent_nodes,
+            ]);
+        } else {
+            $stmt_type = Type::getBool();
         }
 
-        $statements_analyzer->node_data->setType($stmt, Type::getBool());
+        $statements_analyzer->node_data->setType($stmt, $stmt_type);
     }
 }
diff --git a/tests/TypeReconciliation/EmptyTest.php b/tests/TypeReconciliation/EmptyTest.php
index c79918044..944ae2218 100644
--- a/tests/TypeReconciliation/EmptyTest.php
+++ b/tests/TypeReconciliation/EmptyTest.php
@@ -612,6 +612,14 @@ class EmptyTest extends TestCase
                     '$GLOBALS[\'sql_query\']===' => 'string',
                 ],
             ],
+            'emptyLiteralTrueFalse' => [
+                'code' => '<?php
+                    $b = "asdf";
+                    $x = !empty($b);',
+                'assertions' => [
+                    '$x===' => 'true',
+                ],
+            ],
         ];
     }
 
@@ -720,6 +728,30 @@ class EmptyTest extends TestCase
                     }',
                 'error_message' => 'LessSpecificReturnStatement',
             ],
+            'impossibleEmptyOnFalsyFunctionCall' => [
+                'code' => '<?php
+                    /** @return false|null */
+                    function bar() {
+                        return rand(0, 5) ? null : false;
+                    }
+
+                    if (!empty(bar())) {
+                        echo "abc";
+                    }',
+                'error_message' => 'DocblockTypeContradiction',
+            ],
+            'redundantEmptyOnFalsyFunctionCall' => [
+                'code' => '<?php
+                    /** @return false|null */
+                    function bar() {
+                        return rand(0, 5) ? null : false;
+                    }
+
+                    if (empty(bar())) {
+                        echo "abc";
+                    }',
+                'error_message' => 'RedundantConditionGivenDocblockType',
+            ],
         ];
     }
 }