diff --git a/compiler/backend/src/org/jetbrains/kotlin/codegen/inline/InlineCodegen.kt b/compiler/backend/src/org/jetbrains/kotlin/codegen/inline/InlineCodegen.kt
index 2308c3774ee..91e9bbd4555 100644
--- a/compiler/backend/src/org/jetbrains/kotlin/codegen/inline/InlineCodegen.kt
+++ b/compiler/backend/src/org/jetbrains/kotlin/codegen/inline/InlineCodegen.kt
@@ -231,12 +231,6 @@ abstract class InlineCodegen<out T : BaseExpressionCodegen>(
         //through generation captured parameters will be added to invocationParamBuilder
         putClosureParametersOnStack()
 
-        val shouldSpillStack = !canSkipStackSpillingOnInline(node)
-
-        if (shouldSpillStack) {
-            addInlineMarker(codegen.v, true)
-        }
-
         val parameters = invocationParamBuilder.buildParameters()
 
         val info = RootInliningContext(
@@ -271,16 +265,21 @@ abstract class InlineCodegen<out T : BaseExpressionCodegen>(
             removeFinallyMarkers(adapter)
         }
 
-        adapter.accept(MethodBodyVisitor(codegen.v))
+        // In case `codegen.v` is `<clinit>`, initializer for the `$assertionsDisabled` field
+        // needs to be inserted before the code that actually uses it.
+        generateAssertFieldIfNeeded(info)
 
+        val shouldSpillStack = !canSkipStackSpillingOnInline(node)
+        if (shouldSpillStack) {
+            addInlineMarker(codegen.v, true)
+        }
+        adapter.accept(MethodBodyVisitor(codegen.v))
         if (shouldSpillStack) {
             addInlineMarker(codegen.v, false)
         }
 
         defaultSourceMapper.callSiteMarker = null
 
-        generateAssertFieldIfNeeded(info)
-
         return result
     }
 
diff --git a/compiler/testData/codegen/boxInline/assert/jvmClassInitializer.kt b/compiler/testData/codegen/boxInline/assert/jvmClassInitializer.kt
new file mode 100644
index 00000000000..4459ad7884c
--- /dev/null
+++ b/compiler/testData/codegen/boxInline/assert/jvmClassInitializer.kt
@@ -0,0 +1,41 @@
+// TARGET_BACKEND: JVM
+// IGNORE_BACKEND: JVM_IR
+// IGNORE_BACKEND_MULTI_MODULE: JVM_IR
+// FILE: inline.kt
+// KOTLIN_CONFIGURATION_FLAGS: ASSERTIONS_MODE=jvm
+// WITH_RUNTIME
+// FULL_JDK
+package test
+
+class A {
+    inline fun doAssert() {
+        assert(false)
+    }
+}
+
+// FILE: inlineSite.kt
+// KOTLIN_CONFIGURATION_FLAGS: ASSERTIONS_MODE=jvm
+import test.*
+
+class B {
+    companion object {
+        @JvmField
+        val triggered: Boolean = try {
+            A().doAssert()
+            false
+        } catch (e: AssertionError) {
+            true
+        }
+    }
+}
+
+class Dummy
+
+fun box(): String {
+    val loader = Dummy::class.java.classLoader
+    loader.setDefaultAssertionStatus(false)
+    return if (loader.loadClass("B").getField("triggered").get(null) == true)
+        "FAIL: assertion triggered"
+    else
+        "OK"
+}
diff --git a/compiler/tests/org/jetbrains/kotlin/codegen/BlackBoxInlineCodegenTestGenerated.java b/compiler/tests/org/jetbrains/kotlin/codegen/BlackBoxInlineCodegenTestGenerated.java
index 27b3cb9e0a9..62ec4ab3561 100644
--- a/compiler/tests/org/jetbrains/kotlin/codegen/BlackBoxInlineCodegenTestGenerated.java
+++ b/compiler/tests/org/jetbrains/kotlin/codegen/BlackBoxInlineCodegenTestGenerated.java
@@ -640,6 +640,11 @@ public class BlackBoxInlineCodegenTestGenerated extends AbstractBlackBoxInlineCo
             runTest("compiler/testData/codegen/boxInline/assert/jvmAssertInlineLambda.kt");
         }
 
+        @TestMetadata("jvmClassInitializer.kt")
+        public void testJvmClassInitializer() throws Exception {
+            runTest("compiler/testData/codegen/boxInline/assert/jvmClassInitializer.kt");
+        }
+
         @TestMetadata("jvmCompanion.kt")
         public void testJvmCompanion() throws Exception {
             runTest("compiler/testData/codegen/boxInline/assert/jvmCompanion.kt");
diff --git a/compiler/tests/org/jetbrains/kotlin/codegen/CompileKotlinAgainstInlineKotlinTestGenerated.java b/compiler/tests/org/jetbrains/kotlin/codegen/CompileKotlinAgainstInlineKotlinTestGenerated.java
index 55dc9663bff..ac81eda295b 100644
--- a/compiler/tests/org/jetbrains/kotlin/codegen/CompileKotlinAgainstInlineKotlinTestGenerated.java
+++ b/compiler/tests/org/jetbrains/kotlin/codegen/CompileKotlinAgainstInlineKotlinTestGenerated.java
@@ -640,6 +640,11 @@ public class CompileKotlinAgainstInlineKotlinTestGenerated extends AbstractCompi
             runTest("compiler/testData/codegen/boxInline/assert/jvmAssertInlineLambda.kt");
         }
 
+        @TestMetadata("jvmClassInitializer.kt")
+        public void testJvmClassInitializer() throws Exception {
+            runTest("compiler/testData/codegen/boxInline/assert/jvmClassInitializer.kt");
+        }
+
         @TestMetadata("jvmCompanion.kt")
         public void testJvmCompanion() throws Exception {
             runTest("compiler/testData/codegen/boxInline/assert/jvmCompanion.kt");
diff --git a/compiler/tests/org/jetbrains/kotlin/codegen/ir/IrBlackBoxInlineCodegenTestGenerated.java b/compiler/tests/org/jetbrains/kotlin/codegen/ir/IrBlackBoxInlineCodegenTestGenerated.java
index cdabfa2b0e1..26a85313ae9 100644
--- a/compiler/tests/org/jetbrains/kotlin/codegen/ir/IrBlackBoxInlineCodegenTestGenerated.java
+++ b/compiler/tests/org/jetbrains/kotlin/codegen/ir/IrBlackBoxInlineCodegenTestGenerated.java
@@ -640,6 +640,11 @@ public class IrBlackBoxInlineCodegenTestGenerated extends AbstractIrBlackBoxInli
             runTest("compiler/testData/codegen/boxInline/assert/jvmAssertInlineLambda.kt");
         }
 
+        @TestMetadata("jvmClassInitializer.kt")
+        public void testJvmClassInitializer() throws Exception {
+            runTest("compiler/testData/codegen/boxInline/assert/jvmClassInitializer.kt");
+        }
+
         @TestMetadata("jvmCompanion.kt")
         public void testJvmCompanion() throws Exception {
             runTest("compiler/testData/codegen/boxInline/assert/jvmCompanion.kt");
diff --git a/compiler/tests/org/jetbrains/kotlin/codegen/ir/IrCompileKotlinAgainstInlineKotlinTestGenerated.java b/compiler/tests/org/jetbrains/kotlin/codegen/ir/IrCompileKotlinAgainstInlineKotlinTestGenerated.java
index 3098880f328..0a4af37ec62 100644
--- a/compiler/tests/org/jetbrains/kotlin/codegen/ir/IrCompileKotlinAgainstInlineKotlinTestGenerated.java
+++ b/compiler/tests/org/jetbrains/kotlin/codegen/ir/IrCompileKotlinAgainstInlineKotlinTestGenerated.java
@@ -640,6 +640,11 @@ public class IrCompileKotlinAgainstInlineKotlinTestGenerated extends AbstractIrC
             runTest("compiler/testData/codegen/boxInline/assert/jvmAssertInlineLambda.kt");
         }
 
+        @TestMetadata("jvmClassInitializer.kt")
+        public void testJvmClassInitializer() throws Exception {
+            runTest("compiler/testData/codegen/boxInline/assert/jvmClassInitializer.kt");
+        }
+
         @TestMetadata("jvmCompanion.kt")
         public void testJvmCompanion() throws Exception {
             runTest("compiler/testData/codegen/boxInline/assert/jvmCompanion.kt");