diff --git a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosticCompilerTestFE10TestdataTestGenerated.java b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosticCompilerTestFE10TestdataTestGenerated.java
index e4bb17f14ba..89e5ac41730 100644
--- a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosticCompilerTestFE10TestdataTestGenerated.java
+++ b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/DiagnosticCompilerTestFE10TestdataTestGenerated.java
@@ -15276,6 +15276,12 @@ public class DiagnosticCompilerTestFE10TestdataTestGenerated extends AbstractDia
                 runTest("compiler/testData/diagnostics/tests/inference/annotatedUnderscoredTypeArgument.kt");
             }
 
+            @Test
+            @TestMetadata("assertThatInNumerousIf.kt")
+            public void testAssertThatInNumerousIf() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.kt");
+            }
+
             @Test
             @TestMetadata("cannotCompleteResolveAmbiguity.kt")
             public void testCannotCompleteResolveAmbiguity() throws Exception {
diff --git a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated.java b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated.java
index 015a005828a..7f483f470a4 100644
--- a/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated.java
+++ b/analysis/low-level-api-fir/tests/org/jetbrains/kotlin/analysis/low/level/api/fir/diagnostic/compiler/based/LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated.java
@@ -15276,6 +15276,12 @@ public class LLFirPreresolvedReversedDiagnosticCompilerFE10TestDataTestGenerated
                 runTest("compiler/testData/diagnostics/tests/inference/annotatedUnderscoredTypeArgument.kt");
             }
 
+            @Test
+            @TestMetadata("assertThatInNumerousIf.kt")
+            public void testAssertThatInNumerousIf() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.kt");
+            }
+
             @Test
             @TestMetadata("cannotCompleteResolveAmbiguity.kt")
             public void testCannotCompleteResolveAmbiguity() throws Exception {
diff --git a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirLightTreeOldFrontendDiagnosticsTestGenerated.java b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirLightTreeOldFrontendDiagnosticsTestGenerated.java
index 58a1ad3b391..2a2c5a9f626 100644
--- a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirLightTreeOldFrontendDiagnosticsTestGenerated.java
+++ b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirLightTreeOldFrontendDiagnosticsTestGenerated.java
@@ -15276,6 +15276,12 @@ public class FirLightTreeOldFrontendDiagnosticsTestGenerated extends AbstractFir
                 runTest("compiler/testData/diagnostics/tests/inference/annotatedUnderscoredTypeArgument.kt");
             }
 
+            @Test
+            @TestMetadata("assertThatInNumerousIf.kt")
+            public void testAssertThatInNumerousIf() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.kt");
+            }
+
             @Test
             @TestMetadata("cannotCompleteResolveAmbiguity.kt")
             public void testCannotCompleteResolveAmbiguity() throws Exception {
diff --git a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirPsiOldFrontendDiagnosticsTestGenerated.java b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirPsiOldFrontendDiagnosticsTestGenerated.java
index 09e06b617b6..9663262c530 100644
--- a/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirPsiOldFrontendDiagnosticsTestGenerated.java
+++ b/compiler/fir/analysis-tests/tests-gen/org/jetbrains/kotlin/test/runners/FirPsiOldFrontendDiagnosticsTestGenerated.java
@@ -15282,6 +15282,12 @@ public class FirPsiOldFrontendDiagnosticsTestGenerated extends AbstractFirPsiDia
                 runTest("compiler/testData/diagnostics/tests/inference/annotatedUnderscoredTypeArgument.kt");
             }
 
+            @Test
+            @TestMetadata("assertThatInNumerousIf.kt")
+            public void testAssertThatInNumerousIf() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.kt");
+            }
+
             @Test
             @TestMetadata("cannotCompleteResolveAmbiguity.kt")
             public void testCannotCompleteResolveAmbiguity() throws Exception {
diff --git a/compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.fir.kt b/compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.fir.kt
new file mode 100644
index 00000000000..515b892f341
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.fir.kt
@@ -0,0 +1,85 @@
+// ISSUE: KT-60581
+// WITH_STDLIB
+
+// ---------------------- AssertJ declarations --------------------------
+// FILE: AbstractAssert.java
+public abstract class AbstractAssert<SELF extends AbstractAssert<SELF, ACTUAL>, ACTUAL> {}
+
+// FILE: EnumerableAssert.java
+public interface EnumerableAssert<SELF extends EnumerableAssert<SELF, ELEMENT>, ELEMENT> {}
+
+// FILE: ObjectEnumerableAssert.java
+public interface ObjectEnumerableAssert<SELF extends ObjectEnumerableAssert<SELF, ELEMENT>, ELEMENT>
+extends EnumerableAssert<SELF, ELEMENT> {}
+
+// FILE: IndexedObjectEnumerableAssert.java
+public interface IndexedObjectEnumerableAssert<SELF extends IndexedObjectEnumerableAssert<SELF, ELEMENT>, ELEMENT>
+extends ObjectEnumerableAssert<SELF, ELEMENT> {}
+
+// FILE: AbstractIterableAssert.java
+public abstract class AbstractIterableAssert<
+        SELF extends AbstractIterableAssert<SELF, ACTUAL, ELEMENT, ELEMENT_ASSERT>,
+ACTUAL extends Iterable<? extends ELEMENT>,
+ELEMENT,
+ELEMENT_ASSERT extends AbstractAssert<ELEMENT_ASSERT, ELEMENT>>
+extends AbstractAssert<SELF, ACTUAL> implements ObjectEnumerableAssert<SELF, ELEMENT> {}
+
+// FILE: AbstractListAssert.java
+public abstract class AbstractListAssert<
+        SELF extends AbstractListAssert<SELF, ACTUAL, ELEMENT, ELEMENT_ASSERT>,
+ACTUAL extends List<? extends ELEMENT>,
+ELEMENT,
+ELEMENT_ASSERT extends AbstractAssert<ELEMENT_ASSERT, ELEMENT>>
+extends AbstractIterableAssert<SELF, ACTUAL, ELEMENT, ELEMENT_ASSERT>
+implements IndexedObjectEnumerableAssert<SELF, ELEMENT> {
+    SELF isNotEmpty() {
+        return null;
+    }
+}
+
+// FILE: ListAssert.java
+public class ListAssert<ELEMENT> extends AbstractListAssert<ListAssert<ELEMENT>, List<? extends ELEMENT>, ELEMENT, ObjectAssert<ELEMENT>> {}
+
+// FILE: AbstractCharSequenceAssert.java
+public abstract class AbstractCharSequenceAssert<SELF extends AbstractCharSequenceAssert<SELF, ACTUAL>, ACTUAL extends CharSequence>
+extends AbstractAssert<SELF, ACTUAL> implements EnumerableAssert<SELF, Character> {}
+
+// FILE: AbstractStringAssert.java
+public class AbstractStringAssert<SELF extends AbstractStringAssert<SELF>> extends AbstractCharSequenceAssert<SELF, String> {
+    public SELF isEqualTo(String expected) {
+        return null;
+    }
+}
+
+// FILE: StringAssert.java
+public class StringAssert extends AbstractStringAssert<StringAssert> {}
+
+// FILE: test/Assertions.java
+
+import java.util.List;
+
+public class Assertions {
+    public static <ELEMENT> ListAssert<ELEMENT> assertThat(java.util.List<? extends ELEMENT> actual) {
+        return null;
+    }
+
+    public static AbstractStringAssert<?> assertThat(String actual) {
+        return null;
+    }
+}
+
+// FILE: foo.kt
+
+fun test() {
+    val sessionIds = listOf("")
+    val directSessionIds = listOf("")
+    <!NEW_INFERENCE_ERROR!>if (true) {
+        if (true) {
+            Assertions.assertThat(sessionIds[0])
+        } else {
+            Assertions.assertThat(directSessionIds)
+        }
+    } else {
+        Assertions.assertThat(sessionIds)
+    }<!>
+}
diff --git a/compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.kt b/compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.kt
new file mode 100644
index 00000000000..aec55a1794b
--- /dev/null
+++ b/compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.kt
@@ -0,0 +1,85 @@
+// ISSUE: KT-60581
+// WITH_STDLIB
+
+// ---------------------- AssertJ declarations --------------------------
+// FILE: AbstractAssert.java
+public abstract class AbstractAssert<SELF extends AbstractAssert<SELF, ACTUAL>, ACTUAL> {}
+
+// FILE: EnumerableAssert.java
+public interface EnumerableAssert<SELF extends EnumerableAssert<SELF, ELEMENT>, ELEMENT> {}
+
+// FILE: ObjectEnumerableAssert.java
+public interface ObjectEnumerableAssert<SELF extends ObjectEnumerableAssert<SELF, ELEMENT>, ELEMENT>
+extends EnumerableAssert<SELF, ELEMENT> {}
+
+// FILE: IndexedObjectEnumerableAssert.java
+public interface IndexedObjectEnumerableAssert<SELF extends IndexedObjectEnumerableAssert<SELF, ELEMENT>, ELEMENT>
+extends ObjectEnumerableAssert<SELF, ELEMENT> {}
+
+// FILE: AbstractIterableAssert.java
+public abstract class AbstractIterableAssert<
+        SELF extends AbstractIterableAssert<SELF, ACTUAL, ELEMENT, ELEMENT_ASSERT>,
+ACTUAL extends Iterable<? extends ELEMENT>,
+ELEMENT,
+ELEMENT_ASSERT extends AbstractAssert<ELEMENT_ASSERT, ELEMENT>>
+extends AbstractAssert<SELF, ACTUAL> implements ObjectEnumerableAssert<SELF, ELEMENT> {}
+
+// FILE: AbstractListAssert.java
+public abstract class AbstractListAssert<
+        SELF extends AbstractListAssert<SELF, ACTUAL, ELEMENT, ELEMENT_ASSERT>,
+ACTUAL extends List<? extends ELEMENT>,
+ELEMENT,
+ELEMENT_ASSERT extends AbstractAssert<ELEMENT_ASSERT, ELEMENT>>
+extends AbstractIterableAssert<SELF, ACTUAL, ELEMENT, ELEMENT_ASSERT>
+implements IndexedObjectEnumerableAssert<SELF, ELEMENT> {
+    SELF isNotEmpty() {
+        return null;
+    }
+}
+
+// FILE: ListAssert.java
+public class ListAssert<ELEMENT> extends AbstractListAssert<ListAssert<ELEMENT>, List<? extends ELEMENT>, ELEMENT, ObjectAssert<ELEMENT>> {}
+
+// FILE: AbstractCharSequenceAssert.java
+public abstract class AbstractCharSequenceAssert<SELF extends AbstractCharSequenceAssert<SELF, ACTUAL>, ACTUAL extends CharSequence>
+extends AbstractAssert<SELF, ACTUAL> implements EnumerableAssert<SELF, Character> {}
+
+// FILE: AbstractStringAssert.java
+public class AbstractStringAssert<SELF extends AbstractStringAssert<SELF>> extends AbstractCharSequenceAssert<SELF, String> {
+    public SELF isEqualTo(String expected) {
+        return null;
+    }
+}
+
+// FILE: StringAssert.java
+public class StringAssert extends AbstractStringAssert<StringAssert> {}
+
+// FILE: test/Assertions.java
+
+import java.util.List;
+
+public class Assertions {
+    public static <ELEMENT> ListAssert<ELEMENT> assertThat(java.util.List<? extends ELEMENT> actual) {
+        return null;
+    }
+
+    public static AbstractStringAssert<?> assertThat(String actual) {
+        return null;
+    }
+}
+
+// FILE: foo.kt
+
+fun test() {
+    val sessionIds = listOf("")
+    val directSessionIds = listOf("")
+    if (true) {
+        if (true) {
+            Assertions.assertThat(sessionIds[0])
+        } else {
+            Assertions.assertThat(directSessionIds)
+        }
+    } else {
+        Assertions.assertThat(sessionIds)
+    }
+}
diff --git a/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/DiagnosticTestGenerated.java b/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/DiagnosticTestGenerated.java
index 4175a382d7b..b1b2fb4b8e1 100644
--- a/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/DiagnosticTestGenerated.java
+++ b/compiler/tests-common-new/tests-gen/org/jetbrains/kotlin/test/runners/DiagnosticTestGenerated.java
@@ -15282,6 +15282,12 @@ public class DiagnosticTestGenerated extends AbstractDiagnosticTest {
                 runTest("compiler/testData/diagnostics/tests/inference/annotatedUnderscoredTypeArgument.kt");
             }
 
+            @Test
+            @TestMetadata("assertThatInNumerousIf.kt")
+            public void testAssertThatInNumerousIf() throws Exception {
+                runTest("compiler/testData/diagnostics/tests/inference/assertThatInNumerousIf.kt");
+            }
+
             @Test
             @TestMetadata("cannotCompleteResolveAmbiguity.kt")
             public void testCannotCompleteResolveAmbiguity() throws Exception {