diff --git a/core/src/main/kotlin/io/specmatic/core/HttpHeadersPattern.kt b/core/src/main/kotlin/io/specmatic/core/HttpHeadersPattern.kt
index 87f6c4148..224289230 100644
--- a/core/src/main/kotlin/io/specmatic/core/HttpHeadersPattern.kt
+++ b/core/src/main/kotlin/io/specmatic/core/HttpHeadersPattern.kt
@@ -227,7 +227,7 @@ data class HttpHeadersPattern(
                 .filter { exampleHeaderName -> !specPattern.containsKey(exampleHeaderName) && !specPattern.containsKey("${exampleHeaderName}?") }
                 .filter { exampleHeaderName -> exampleHeaderName.lowercase() !in getHeadersToExcludeNotInExamples(row.requestExample) }
                 .filter { exampleHeaderName -> exampleHeaderName !in row.requestExample.metadata.securityHeaderNames }
-                .associateWith { StringPattern() }
+                .associateWith { exampleHeaderName -> ExactValuePattern(StringValue(row.requestExample.headers.getValue(exampleHeaderName))) }
         } else {
             emptyMap()
         }
diff --git a/core/src/test/kotlin/integration_tests/ExtensibleHeadersTest.kt b/core/src/test/kotlin/integration_tests/ExtensibleHeadersTest.kt
index c93be630e..b3c4d2b69 100644
--- a/core/src/test/kotlin/integration_tests/ExtensibleHeadersTest.kt
+++ b/core/src/test/kotlin/integration_tests/ExtensibleHeadersTest.kt
@@ -346,6 +346,7 @@ components:
 
         val results = feature.executeTests(object : TestExecutor {
             override fun execute(request: HttpRequest): HttpResponse {
+                assertThat(request.headers).containsEntry("Authenticate", "abc123")
                 return HttpResponse.ok(parsedJSONObject("""{"greeting": "Hi!"}""")).also {
                     println(request.toLogString())
                     println(it.toLogString())
@@ -366,6 +367,7 @@ components:
 
         val results = feature.executeTests(object : TestExecutor {
             override fun execute(request: HttpRequest): HttpResponse {
+                assertThat(request.headers).containsEntry("Authenticate", "abc123")
                 return HttpResponse.ok(parsedJSONObject("""{"greeting": "Hi!"}""")).also {
                     println(request.toLogString())
                     println(it.toLogString())
@@ -386,6 +388,7 @@ components:
 
         val results = feature.executeTests(object : TestExecutor {
             override fun execute(request: HttpRequest): HttpResponse {
+                assertThat(request.headers).containsEntry("Authenticate", "abc123")
                 return HttpResponse.ok(parsedJSONObject("""{"greeting": "Hi!"}""")).also {
                     println(request.toLogString())
                     println(it.toLogString())
diff --git a/core/src/test/kotlin/io/specmatic/conversions/ExampleFromFileTest.kt b/core/src/test/kotlin/io/specmatic/conversions/ExampleFromFileTest.kt
index ae3e83b59..3800dc9cd 100644
--- a/core/src/test/kotlin/io/specmatic/conversions/ExampleFromFileTest.kt
+++ b/core/src/test/kotlin/io/specmatic/conversions/ExampleFromFileTest.kt
@@ -1,6 +1,8 @@
 package io.specmatic.conversions
 
+import io.specmatic.core.HttpHeadersPattern
 import io.specmatic.core.NoBodyValue
+import io.specmatic.core.Resolver
 import io.specmatic.core.SpecmaticConfig
 import io.specmatic.core.pattern.parsedJSONObject
 import org.assertj.core.api.Assertions.assertThat
@@ -135,5 +137,8 @@ class ExampleFromFileTest {
             example.toRow(SpecmaticConfig(additionalExampleParamsFilePath = "src/test/resources/additionalParamsFile.json"))
 
         assertThat(row.requestExample?.headers.orEmpty()).containsEntry("X-Tra", "info")
+
+        val generatedHeaders = HttpHeadersPattern().newBasedOn(row, Resolver()).first().value.generate(Resolver())
+        assertThat(generatedHeaders).containsEntry("X-Tra", "info")
     }
 }
\ No newline at end of file