diff --git a/src/Analyser/MutatingScope.php b/src/Analyser/MutatingScope.php
index 122340cc27b..1046029b244 100644
--- a/src/Analyser/MutatingScope.php
+++ b/src/Analyser/MutatingScope.php
@@ -3649,6 +3649,15 @@ private function createConditionalExpressions(
 				) {
 					continue;
 				}
+				if (
+					!array_key_exists($exprString, $theirExpressionTypes)
+					&& !$holder->getExpr() instanceof Variable
+					&& array_key_exists($guardExprString, $theirExpressionTypes)
+					&& $theirExpressionTypes[$guardExprString]->getCertainty()->yes()
+					&& !$guardHolder->getType()->isSuperTypeOf($theirExpressionTypes[$guardExprString]->getType())->no()
+				) {
+					continue;
+				}
 				$conditionalExpression = new ConditionalExpressionHolder([$guardExprString => $guardHolder], $holder);
 				$conditionalExpressions[$exprString][$conditionalExpression->getKey()] = $conditionalExpression;
 			}
diff --git a/tests/PHPStan/Analyser/nsrt/bug-14469.php b/tests/PHPStan/Analyser/nsrt/bug-14469.php
new file mode 100644
index 00000000000..67bff59378f
--- /dev/null
+++ b/tests/PHPStan/Analyser/nsrt/bug-14469.php
@@ -0,0 +1,35 @@
+<?php
+
+namespace Bug14469Nsrt;
+
+use function PHPStan\Testing\assertType;
+
+function t(array $R, bool $var1, object $user): void {
+	$aa = null;
+
+	if ($var1) {
+		$aa = $user->id === 10 ? 2 : null;
+	} elseif ($R['aa']) {
+		$aa = $R['aa'];
+	}
+
+	if ($aa) {
+		assertType('mixed', $R['aa']);
+	}
+}
+
+/** @param mixed $input */
+function variableEquivalent($input, bool $var1, object $user): void {
+	$aa = null;
+	$bb = $input;
+
+	if ($var1) {
+		$aa = $user->id === 10 ? 2 : null;
+	} elseif ($bb) {
+		$aa = $bb;
+	}
+
+	if ($aa) {
+		assertType('mixed', $bb);
+	}
+}
diff --git a/tests/PHPStan/Rules/Comparison/BooleanNotConstantConditionRuleTest.php b/tests/PHPStan/Rules/Comparison/BooleanNotConstantConditionRuleTest.php
index 3cf3f2a8bbc..ee1d1ff12fe 100644
--- a/tests/PHPStan/Rules/Comparison/BooleanNotConstantConditionRuleTest.php
+++ b/tests/PHPStan/Rules/Comparison/BooleanNotConstantConditionRuleTest.php
@@ -236,4 +236,10 @@ public function testBug6702(): void
 		$this->analyse([__DIR__ . '/data/bug-6702.php'], []);
 	}
 
+	public function testBug14469(): void
+	{
+		$this->treatPhpDocTypesAsCertain = true;
+		$this->analyse([__DIR__ . '/data/bug-14469.php'], []);
+	}
+
 }
diff --git a/tests/PHPStan/Rules/Comparison/data/bug-14469.php b/tests/PHPStan/Rules/Comparison/data/bug-14469.php
new file mode 100644
index 00000000000..66c6a98aa07
--- /dev/null
+++ b/tests/PHPStan/Rules/Comparison/data/bug-14469.php
@@ -0,0 +1,91 @@
+<?php
+
+namespace Bug14469;
+
+function t(array $R, bool $var1, object $user, bool $is): array {
+    $aa = null;
+
+    if ($var1) {
+        $aa = $user->id  === 10 ? 2 : null;
+    } elseif ($R['aa']) {
+        $aa = $R['aa'];
+    }
+
+    if ($aa) {
+        if (!$R['aa']) {
+            return [];
+        }
+    }
+	return $R;
+}
+
+/** Property fetch variant */
+function propertyFetch(object $obj, bool $var1, object $user): void {
+    $aa = null;
+
+    if ($var1) {
+        $aa = $user->id === 10 ? 2 : null;
+    } elseif ($obj->prop) {
+        $aa = $obj->prop;
+    }
+
+    if ($aa) {
+        if (!$obj->prop) {
+            return;
+        }
+    }
+}
+
+/** Nested array fetch variant */
+function nestedArrayFetch(array $R, bool $var1, object $user): void {
+    $aa = null;
+
+    if ($var1) {
+        $aa = $user->id === 10 ? 2 : null;
+    } elseif ($R['a']['b']) {
+        $aa = $R['a']['b'];
+    }
+
+    if ($aa) {
+        if (!$R['a']['b']) {
+            return;
+        }
+    }
+}
+
+/** Multiple elseif branches */
+function multipleElseif(array $R, bool $var1, bool $var2, object $user): void {
+    $aa = null;
+
+    if ($var1) {
+        $aa = $user->id === 10 ? 2 : null;
+    } elseif ($var2) {
+        $aa = 5;
+    } elseif ($R['aa']) {
+        $aa = $R['aa'];
+    }
+
+    if ($aa) {
+        if (!$R['aa']) {
+            return;
+        }
+    }
+}
+
+/** @param mixed $input */
+function variableEquivalent(bool $var1, object $user, $input): void {
+	$aa = null;
+	$bb = $input;
+
+	if ($var1) {
+		$aa = $user->id === 10 ? 2 : null;
+	} elseif ($bb) {
+		$aa = $bb;
+	}
+
+	if ($aa) {
+		if (!$bb) {
+			return;
+		}
+	}
+}