diff --git a/tools/kotlin-native-gradle-plugin/src/test/groovy/org/jetbrains/kotlin/gradle/plugin/test/IncrementalSpecification.groovy b/tools/kotlin-native-gradle-plugin/src/test/groovy/org/jetbrains/kotlin/gradle/plugin/test/IncrementalSpecification.groovy
index 06d6452936a..5efb6661054 100644
--- a/tools/kotlin-native-gradle-plugin/src/test/groovy/org/jetbrains/kotlin/gradle/plugin/test/IncrementalSpecification.groovy
+++ b/tools/kotlin-native-gradle-plugin/src/test/groovy/org/jetbrains/kotlin/gradle/plugin/test/IncrementalSpecification.groovy
@@ -196,6 +196,19 @@ class IncrementalSpecification extends BaseKonanSpecification {
         "noDefaultLibs"      | "true"
     }
 
+    def 'headerFilterAdditionalSearchPrefix change should cause recompilation and interop reprocessing'() {
+        when:
+        def project = KonanProject.createWithInterop(projectDirectory) { KonanProject it ->
+            it.defFiles.first().write("headers = stdio.h\nheaderFilter = stdio.h")
+        }
+        def results = buildTwice(project) { KonanProject it ->
+            it.addSetting(KonanProject.DEFAULT_INTEROP_NAME, "headerFilterAdditionalSearchPrefix", "'.'")
+        }
+
+        then:
+        recompilationAndInteropProcessingHappened(*results)
+    }
+
     def 'defFile change for an interop task should cause recompilation and interop reprocessing'() {
         when:
         def project = KonanProject.createWithInterop(projectDirectory, ArtifactType.LIBRARY)
diff --git a/tools/kotlin-native-gradle-plugin/src/test/groovy/org/jetbrains/kotlin/gradle/plugin/test/TaskSpecification.groovy b/tools/kotlin-native-gradle-plugin/src/test/groovy/org/jetbrains/kotlin/gradle/plugin/test/TaskSpecification.groovy
index ebdbc1d8255..34ef565ab6a 100644
--- a/tools/kotlin-native-gradle-plugin/src/test/groovy/org/jetbrains/kotlin/gradle/plugin/test/TaskSpecification.groovy
+++ b/tools/kotlin-native-gradle-plugin/src/test/groovy/org/jetbrains/kotlin/gradle/plugin/test/TaskSpecification.groovy
@@ -34,6 +34,22 @@ class TaskSpecification extends BaseKonanSpecification {
         result.output.findAll(~/BACKEND:\s+\d+\s+msec/).size() == 1
     }
 
+    def 'Plugin should support headerFilterAdditionalSearchPrefix option for cinterop'() {
+        expect:
+        def project = KonanProject.createEmpty(projectDirectory) { KonanProject it ->
+            it.addCompilerArtifact("interopLib", "headers=foo.h\nheaderFilter=foo.h bar.h", ArtifactType.INTEROP)
+            it.generateSrcFile(it.projectPath, "foo.h", "#include <bar.h>")
+            def fooDir = it.projectPath.resolve("foo")
+            it.generateSrcFile(fooDir, "bar.h", "const int foo = 5;")
+            it.addSetting("interopLib", "headerFilterAdditionalSearchPrefix", fooDir.toFile())
+            it.addSetting("interopLib", "headerFilterAdditionalSearchPrefix", it.projectDir)
+        }
+        project.createRunner().withArguments("build").build()
+        def wrong_path = project.createFile("wrong_path", "")
+        project.addSetting("interopLib", "headerFilterAdditionalSearchPrefix", wrong_path)
+        project.createRunner().withArguments("build").buildAndFail()
+    }
+
     BuildResult failOnPropertyAccess(KonanProject project, String property) {
          project.buildFile.append("""
             task testTask(type: DefaultTask) {