diff --git a/CHANGELOG.md b/CHANGELOG.md
index cccf7a05d..47ffeebbb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@ Please add your entries according to this format.
 ### Fixed
 
 * Fixed not setting request body type correctly [#538].
+* Fixed request headers not being redacted in case of failures [#545].
 
 ### Removed
 
diff --git a/library/src/main/java/com/chuckerteam/chucker/api/ChuckerInterceptor.kt b/library/src/main/java/com/chuckerteam/chucker/api/ChuckerInterceptor.kt
index bb5b7f19b..f58eb8e63 100755
--- a/library/src/main/java/com/chuckerteam/chucker/api/ChuckerInterceptor.kt
+++ b/library/src/main/java/com/chuckerteam/chucker/api/ChuckerInterceptor.kt
@@ -14,8 +14,8 @@ import com.chuckerteam.chucker.internal.support.contentType
 import com.chuckerteam.chucker.internal.support.hasBody
 import com.chuckerteam.chucker.internal.support.hasSupportedContentEncoding
 import com.chuckerteam.chucker.internal.support.isProbablyPlainText
+import com.chuckerteam.chucker.internal.support.redact
 import com.chuckerteam.chucker.internal.support.uncompress
-import okhttp3.Headers
 import okhttp3.Interceptor
 import okhttp3.Response
 import okhttp3.ResponseBody.Companion.asResponseBody
@@ -52,7 +52,7 @@ public class ChuckerInterceptor private constructor(
     private val cacheDirectoryProvider = builder.cacheDirectoryProvider ?: CacheDirectoryProvider { context.filesDir }
     private val alwaysReadResponseBody = builder.alwaysReadResponseBody
     private val headersToRedact = builder.headersToRedact.toMutableSet()
-    private val requestProcessor = RequestProcessor(context, collector, maxContentLength)
+    private val requestProcessor = RequestProcessor(context, collector, maxContentLength, headersToRedact)
 
     /** Adds [headerName] into [headersToRedact] */
     public fun redactHeader(vararg headerName: String) {
@@ -87,8 +87,8 @@ public class ChuckerInterceptor private constructor(
 
         transaction.apply {
             // includes headers added later in the chain
-            setRequestHeaders(filterHeaders(response.request.headers))
-            setResponseHeaders(filterHeaders(response.headers))
+            setRequestHeaders(response.request.headers.redact(headersToRedact))
+            setResponseHeaders(response.headers.redact(headersToRedact))
 
             isResponseBodyPlainText = responseEncodingIsSupported
             requestDate = response.sentRequestAtMillis
@@ -176,17 +176,6 @@ public class ChuckerInterceptor private constructor(
         }
     }
 
-    /** Overrides all headers from [headersToRedact] with `**` */
-    private fun filterHeaders(headers: Headers): Headers {
-        val builder = headers.newBuilder()
-        for (name in headers.names()) {
-            if (headersToRedact.any { userHeader -> userHeader.equals(name, ignoreCase = true) }) {
-                builder.set(name, "**")
-            }
-        }
-        return builder.build()
-    }
-
     private inner class ChuckerTransactionReportingSinkCallback(
         private val response: Response,
         private val transaction: HttpTransaction
diff --git a/library/src/main/java/com/chuckerteam/chucker/internal/support/OkHttpUtils.kt b/library/src/main/java/com/chuckerteam/chucker/internal/support/OkHttpUtils.kt
index 023bcbceb..8fc5c9c1f 100644
--- a/library/src/main/java/com/chuckerteam/chucker/internal/support/OkHttpUtils.kt
+++ b/library/src/main/java/com/chuckerteam/chucker/internal/support/OkHttpUtils.kt
@@ -64,3 +64,13 @@ internal fun Source.uncompress(headers: Headers) = if (headers.containsGzip) {
 } else {
     this
 }
+
+internal fun Headers.redact(names: Iterable<String>): Headers {
+    val builder = newBuilder()
+    for (name in names()) {
+        if (names.any { userHeader -> userHeader.equals(name, ignoreCase = true) }) {
+            builder[name] = "**"
+        }
+    }
+    return builder.build()
+}
diff --git a/library/src/main/java/com/chuckerteam/chucker/internal/support/RequestProcessor.kt b/library/src/main/java/com/chuckerteam/chucker/internal/support/RequestProcessor.kt
index e5904d473..bd0162e7e 100644
--- a/library/src/main/java/com/chuckerteam/chucker/internal/support/RequestProcessor.kt
+++ b/library/src/main/java/com/chuckerteam/chucker/internal/support/RequestProcessor.kt
@@ -13,6 +13,7 @@ internal class RequestProcessor(
     private val context: Context,
     private val collector: ChuckerCollector,
     private val maxContentLength: Long,
+    private val headersToRedact: Set<String>,
 ) {
     fun process(request: Request, transaction: HttpTransaction): Request {
         processMetadata(request, transaction)
@@ -23,7 +24,7 @@ internal class RequestProcessor(
 
     private fun processMetadata(request: Request, transaction: HttpTransaction) {
         transaction.apply {
-            setRequestHeaders(request.headers)
+            setRequestHeaders(request.headers.redact(headersToRedact))
             populateUrl(request.url)
 
             requestDate = System.currentTimeMillis()
diff --git a/library/src/test/java/com/chuckerteam/chucker/api/ChuckerInterceptorTest.kt b/library/src/test/java/com/chuckerteam/chucker/api/ChuckerInterceptorTest.kt
index 1176301df..975048695 100644
--- a/library/src/test/java/com/chuckerteam/chucker/api/ChuckerInterceptorTest.kt
+++ b/library/src/test/java/com/chuckerteam/chucker/api/ChuckerInterceptorTest.kt
@@ -17,6 +17,7 @@ import okhttp3.RequestBody
 import okhttp3.RequestBody.Companion.toRequestBody
 import okhttp3.mockwebserver.MockResponse
 import okhttp3.mockwebserver.MockWebServer
+import okhttp3.mockwebserver.SocketPolicy
 import okio.Buffer
 import okio.ByteString
 import okio.ByteString.Companion.encodeUtf8
@@ -496,5 +497,30 @@ internal class ChuckerInterceptorTest {
         assertThat(transaction.requestPayloadSize).isEqualTo(request.body!!.contentLength())
     }
 
+    @ParameterizedTest
+    @EnumSource(value = ClientFactory::class)
+    fun requestHeaders_areRedacted_whenServerFails(factory: ClientFactory) {
+        val chuckerInterceptor = ChuckerInterceptorDelegate(
+            maxContentLength = SEGMENT_SIZE,
+            headersToRedact = setOf("Header-To-Redact"),
+            cacheDirectoryProvider = { tempDir },
+        )
+        val client = factory.create(chuckerInterceptor)
+
+        val request = Request.Builder().url(serverUrl).header("Header-To-Redact", "Hello").build()
+        server.enqueue(MockResponse().setSocketPolicy(SocketPolicy.DISCONNECT_AT_START))
+        runCatching { client.newCall(request).execute() }
+
+        val transaction = chuckerInterceptor.expectTransaction()
+        assertThat(transaction.requestHeaders).contains(
+            """
+            |  {
+            |    "name": "Header-To-Redact",
+            |    "value": "**"
+            |  }
+            """.trimMargin()
+        )
+    }
+
     private fun RequestBody.toServerRequest() = Request.Builder().url(serverUrl).post(this).build()
 }