diff --git a/airbyte-cdk/bulk/core/base/src/main/kotlin/io/airbyte/cdk/output/DefaultExceptionClassifier.kt b/airbyte-cdk/bulk/core/base/src/main/kotlin/io/airbyte/cdk/output/DefaultExceptionClassifier.kt
index 71da76a5859f..fc6f09259b1a 100644
--- a/airbyte-cdk/bulk/core/base/src/main/kotlin/io/airbyte/cdk/output/DefaultExceptionClassifier.kt
+++ b/airbyte-cdk/bulk/core/base/src/main/kotlin/io/airbyte/cdk/output/DefaultExceptionClassifier.kt
@@ -22,24 +22,12 @@ class DefaultExceptionClassifier(
 ) : ExceptionClassifier {
 
     override fun classify(e: Throwable): ConnectorError? {
-        return when (val connectorErrorException: ConnectorErrorException? = unwind(e)) {
-            is ConfigErrorException -> ConfigError(connectorErrorException.message!!)
-            is TransientErrorException -> TransientError(connectorErrorException.message!!)
-            is SystemErrorException -> SystemError(connectorErrorException.message)
-            null -> null
+        val unwound: Throwable? = ExceptionClassifier.unwind(e) { it is ConnectorErrorException }
+        return when (unwound) {
+            is ConfigErrorException -> ConfigError(unwound.message!!)
+            is TransientErrorException -> TransientError(unwound.message!!)
+            is SystemErrorException -> SystemError(unwound.message)
+            else -> null
         }
     }
-
-    /** Recursively walks the causes of [e] and returns the last [ConnectorErrorException]. */
-    fun unwind(e: Throwable): ConnectorErrorException? {
-        var connectorErrorException: ConnectorErrorException? = null
-        var unwound: Throwable? = e
-        while (unwound != null) {
-            if (unwound is ConnectorErrorException) {
-                connectorErrorException = unwound
-            }
-            unwound = unwound.cause
-        }
-        return connectorErrorException
-    }
 }
diff --git a/airbyte-cdk/bulk/core/base/src/main/kotlin/io/airbyte/cdk/output/ExceptionClassifier.kt b/airbyte-cdk/bulk/core/base/src/main/kotlin/io/airbyte/cdk/output/ExceptionClassifier.kt
index 0b7e19b44aec..1583a271fb6e 100644
--- a/airbyte-cdk/bulk/core/base/src/main/kotlin/io/airbyte/cdk/output/ExceptionClassifier.kt
+++ b/airbyte-cdk/bulk/core/base/src/main/kotlin/io/airbyte/cdk/output/ExceptionClassifier.kt
@@ -15,6 +15,16 @@ interface ExceptionClassifier : Ordered {
     val orderValue: Int
 
     override fun getOrder(): Int = orderValue
+
+    companion object {
+        fun unwind(e: Throwable, stopUnwind: (Throwable) -> Boolean): Throwable? {
+            var unwound = e
+            while (!stopUnwind(unwound)) {
+                unwound = unwound.cause ?: return null
+            }
+            return unwound
+        }
+    }
 }
 
 /** Each [ConnectorError] subtype corresponds to a [AirbyteErrorTraceMessage.FailureType]. */
@@ -54,10 +64,8 @@ interface RuleBasedExceptionClassifier<T : RuleBasedExceptionClassifier.Rule> :
 
     override fun classify(e: Throwable): ConnectorError? {
         for (rule in rules) {
-            if (!rule.matches(e)) {
-                continue
-            }
-            val message: String = rule.output ?: e.message ?: e.toString()
+            val match: Throwable = ExceptionClassifier.unwind(e, rule::matches) ?: continue
+            val message: String = rule.output ?: match.message ?: match.toString()
             val firstLine: String = if (rule.group == null) message else "${rule.group}: $message"
             val lines: List<String> = listOf(firstLine) + rule.referenceLinks
             val displayMessage: String = lines.joinToString(separator = "\n")
diff --git a/airbyte-cdk/bulk/core/base/src/test/kotlin/io/airbyte/cdk/output/RegexExceptionClassifierTest.kt b/airbyte-cdk/bulk/core/base/src/test/kotlin/io/airbyte/cdk/output/RegexExceptionClassifierTest.kt
index e511d46488ec..2fa23ddd680a 100644
--- a/airbyte-cdk/bulk/core/base/src/test/kotlin/io/airbyte/cdk/output/RegexExceptionClassifierTest.kt
+++ b/airbyte-cdk/bulk/core/base/src/test/kotlin/io/airbyte/cdk/output/RegexExceptionClassifierTest.kt
@@ -80,4 +80,16 @@ class RegexExceptionClassifierTest {
             classifier.classify(RuntimeException("barbaz")),
         )
     }
+
+    @Test
+    fun testRecursiveRuleOrdering() {
+        Assertions.assertEquals(
+            ConfigError("grouped: has foo\nhttps://www.youtube.com/watch?v=xvFZjo5PgG0"),
+            classifier.classify(RuntimeException("quux", RuntimeException("foobarbaz"))),
+        )
+        Assertions.assertEquals(
+            TransientError("barbaz"),
+            classifier.classify(RuntimeException("quux", RuntimeException("barbaz"))),
+        )
+    }
 }
diff --git a/airbyte-cdk/bulk/toolkits/extract-jdbc/src/main/kotlin/io/airbyte/cdk/output/JdbcExceptionClassifier.kt b/airbyte-cdk/bulk/toolkits/extract-jdbc/src/main/kotlin/io/airbyte/cdk/output/JdbcExceptionClassifier.kt
index 806f0c1d10c6..adb8713bde4e 100644
--- a/airbyte-cdk/bulk/toolkits/extract-jdbc/src/main/kotlin/io/airbyte/cdk/output/JdbcExceptionClassifier.kt
+++ b/airbyte-cdk/bulk/toolkits/extract-jdbc/src/main/kotlin/io/airbyte/cdk/output/JdbcExceptionClassifier.kt
@@ -29,15 +29,16 @@ class JdbcExceptionClassifier(
     }
 
     override fun classify(e: Throwable): ConnectorError? {
-        if (e !is SQLException) return null
+        var match: SQLException =
+            ExceptionClassifier.unwind(e) { it is SQLException } as? SQLException ?: return null
         val decoratedMessage: String =
             listOfNotNull(
-                    e.sqlState?.let { "State code: $it" },
-                    e.errorCode.takeIf { it != 0 }?.let { "Error code: $it" },
-                    e.message?.let { "Message: $it" },
+                    match.sqlState?.let { "State code: $it" },
+                    match.errorCode.takeIf { it != 0 }?.let { "Error code: $it" },
+                    match.message?.let { "Message: $it" },
                 )
                 .joinToString(separator = "; ")
-        val decoratedException = SQLException(decoratedMessage, e.sqlState, e.errorCode)
+        val decoratedException = SQLException(decoratedMessage, match.sqlState, match.errorCode)
         val ruleBasedMatch: ConnectorError? = super.classify(decoratedException)
         if (ruleBasedMatch != null) {
             return ruleBasedMatch