diff --git a/plugins/kapt3/kapt3-compiler/src/org/jetbrains/kotlin/kapt3/javac/KaptTreeMaker.kt b/plugins/kapt3/kapt3-compiler/src/org/jetbrains/kotlin/kapt3/javac/KaptTreeMaker.kt
index 5ff19a547be..70e1eda92cc 100644
--- a/plugins/kapt3/kapt3-compiler/src/org/jetbrains/kotlin/kapt3/javac/KaptTreeMaker.kt
+++ b/plugins/kapt3/kapt3-compiler/src/org/jetbrains/kotlin/kapt3/javac/KaptTreeMaker.kt
@@ -113,17 +113,20 @@ class KaptTreeMaker(context: Context, private val kaptContext: KaptContext<*>) :
     }
 
     private inline fun String.iterateDollars(variantHandler: (outerName: String, innerName: String) -> Unit) {
-        var dollarIndex = this.indexOf('$')
-        if (dollarIndex < 0) {
-            variantHandler(this, "")
-            return
-        }
+        var dollarIndex = this.indexOf('$', startIndex = 1)
 
-        while (dollarIndex > 0 && dollarIndex < this.lastIndex) {
-            val outerName = this.take(dollarIndex)
-            val innerName = this.drop(dollarIndex + 1)
+        while (dollarIndex > 0) {
+            val previousSymbol = this[dollarIndex - 1]
+            val nextSymbol = this.getOrNull(dollarIndex + 1)
 
-            variantHandler(outerName, innerName)
+            if (previousSymbol != '.' && nextSymbol != '.') {
+                val outerName = this.take(dollarIndex)
+                val innerName = this.drop(dollarIndex + 1)
+
+                if (outerName.isNotEmpty() && innerName.isNotEmpty()) {
+                    variantHandler(outerName, innerName)
+                }
+            }
 
             dollarIndex = this.indexOf('$', startIndex = dollarIndex + 1)
         }
diff --git a/plugins/kapt3/kapt3-compiler/test/org/jetbrains/kotlin/kapt3/test/ClassFileToSourceStubConverterTestGenerated.java b/plugins/kapt3/kapt3-compiler/test/org/jetbrains/kotlin/kapt3/test/ClassFileToSourceStubConverterTestGenerated.java
index 4906471bc1a..1792ed70f80 100644
--- a/plugins/kapt3/kapt3-compiler/test/org/jetbrains/kotlin/kapt3/test/ClassFileToSourceStubConverterTestGenerated.java
+++ b/plugins/kapt3/kapt3-compiler/test/org/jetbrains/kotlin/kapt3/test/ClassFileToSourceStubConverterTestGenerated.java
@@ -235,6 +235,18 @@ public class ClassFileToSourceStubConverterTestGenerated extends AbstractClassFi
         doTest(fileName);
     }
 
+    @TestMetadata("leadingDollars.kt")
+    public void testLeadingDollars() throws Exception {
+        String fileName = KotlinTestUtils.navigationMetadata("plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars.kt");
+        doTest(fileName);
+    }
+
+    @TestMetadata("leadingDollars2.kt")
+    public void testLeadingDollars2() throws Exception {
+        String fileName = KotlinTestUtils.navigationMetadata("plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars2.kt");
+        doTest(fileName);
+    }
+
     @TestMetadata("mapEntry.kt")
     public void testMapEntry() throws Exception {
         String fileName = KotlinTestUtils.navigationMetadata("plugins/kapt3/kapt3-compiler/testData/converter/mapEntry.kt");
diff --git a/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars.kt b/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars.kt
new file mode 100644
index 00000000000..46b3e8278c0
--- /dev/null
+++ b/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars.kt
@@ -0,0 +1,19 @@
+// CORRECT_ERROR_TYPES
+
+// FILE: $Test.java
+public class $Test {
+    public static class $Inner {}
+}
+
+// FILE: Test$.java
+public class Test$ {
+    public static class Inner$ {}
+}
+
+// FILE: test.kt
+
+package test
+
+fun test(a: `$Test`.`$Inner`) {}
+
+fun test(a: `Test$`.`Inner$`) {}
\ No newline at end of file
diff --git a/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars.txt b/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars.txt
new file mode 100644
index 00000000000..32cfaa38437
--- /dev/null
+++ b/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars.txt
@@ -0,0 +1,52 @@
+public class $Test {
+
+    public $Test() {
+        super();
+    }
+
+    public static class $Inner {
+
+        public $Inner() {
+            super();
+        }
+    }
+}
+
+////////////////////
+
+
+public class Test$ {
+
+    public Test$() {
+        super();
+    }
+
+    public static class Inner$ {
+
+        public Inner$() {
+            super();
+        }
+    }
+}
+
+////////////////////
+
+package test;
+
+import java.lang.System;
+
+@kotlin.Metadata()
+public final class TestKt {
+
+    public TestKt() {
+        super();
+    }
+
+    public static final void test(@org.jetbrains.annotations.NotNull()
+    $Test.$Inner a) {
+    }
+
+    public static final void test(@org.jetbrains.annotations.NotNull()
+    Test$.Inner$ a) {
+    }
+}
diff --git a/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars2.kt b/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars2.kt
new file mode 100644
index 00000000000..3d8ac610100
--- /dev/null
+++ b/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars2.kt
@@ -0,0 +1,16 @@
+// CORRECT_ERROR_TYPES
+
+// FILE: te/st/a/JavaClass
+package te.st.a;
+
+public class JavaClass {}
+
+// FILE: test.kt
+@file:Suppress("UNRESOLVED_REFERENCE")
+package te.st.a
+
+import te.st.a.`$Test`.Inner as MyInner
+import te.st.a.`Test$`.Inner as MyInner2
+import te.st.a.`Test$`.`Inner$` as MyInner3
+
+fun a(a: MyInner) {}
\ No newline at end of file
diff --git a/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars2.txt b/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars2.txt
new file mode 100644
index 00000000000..1639e37c1b7
--- /dev/null
+++ b/plugins/kapt3/kapt3-compiler/testData/converter/leadingDollars2.txt
@@ -0,0 +1,17 @@
+package te.st.a;
+
+import te.st.a.$Test.Inner;
+import te.st.a.Test$.Inner$;
+
+@kotlin.Suppress(names = {"UNRESOLVED_REFERENCE"})
+@kotlin.Metadata()
+public final class TestKt {
+
+    public TestKt() {
+        super();
+    }
+
+    public static final void a(@org.jetbrains.annotations.NotNull()
+    te.st.a.$Test.Inner a) {
+    }
+}