diff --git a/jvm/src/main/scala/com/nawforce/apexlink/org/OrgInfo.scala b/jvm/src/main/scala/com/nawforce/apexlink/org/OrgInfo.scala
index b0ac8fb05..a9ce92b8e 100644
--- a/jvm/src/main/scala/com/nawforce/apexlink/org/OrgInfo.scala
+++ b/jvm/src/main/scala/com/nawforce/apexlink/org/OrgInfo.scala
@@ -14,9 +14,18 @@
 package com.nawforce.apexlink.org
 
 import com.nawforce.apexlink.org.OPM.OrgImpl
-import com.nawforce.pkgforce.diagnostics.{Diagnostic, ERROR_CATEGORY, Issue, MISSING_CATEGORY}
-import com.nawforce.pkgforce.path.PathLocation
+import com.nawforce.pkgforce.diagnostics.{
+  Diagnostic,
+  ERROR_CATEGORY,
+  Issue,
+  LoggerOps,
+  MISSING_CATEGORY
+}
+import com.nawforce.pkgforce.path.{Location, PathLike, PathLocation}
 
+import java.io.{File, PrintWriter, StringWriter}
+import java.nio.file.Files
+import scala.collection.compat.immutable.ArraySeq
 import scala.util.DynamicVariable
 
 /** Access to the 'current' org, this should be deprecated now we have the OPM hierarchy.
@@ -42,4 +51,37 @@ object OrgInfo {
     log(new Issue(pathLocation.path, Diagnostic(MISSING_CATEGORY, pathLocation.location, message)))
   }
 
+  /** Log an exception during processing. If at least one path is provided this logs the
+    * exception against the first. The files are copied to a temporary directory to aid debugging.
+    */
+  private[nawforce] def logException(ex: Throwable, paths: ArraySeq[PathLike]): Unit = {
+    if (paths.isEmpty) {
+      LoggerOps.info("Exception reported against no paths", ex)
+      return
+    }
+
+    try {
+      val writer = new StringWriter
+      writer.append("Validation failed: ")
+      val tempDir = Files.createTempDirectory("apex-ls-log")
+      paths.foreach(path => {
+        val from = new File(path.toString).toPath
+        if (Files.exists(from)) {
+          Files.copy(
+            from,
+            tempDir.resolve(from.getFileName),
+            java.nio.file.StandardCopyOption.REPLACE_EXISTING
+          )
+        }
+      })
+      writer.append("log directory ")
+      writer.append(tempDir.toString)
+      writer.append('\n')
+      ex.printStackTrace(new PrintWriter(writer))
+      log(Issue(ERROR_CATEGORY, PathLocation(paths.head, Location.empty), writer.toString))
+    } catch {
+      case ex: Throwable =>
+        LoggerOps.info("Failed to log an exception", ex)
+    }
+  }
 }
diff --git a/jvm/src/main/scala/com/nawforce/apexlink/types/core/TypeDeclaration.scala b/jvm/src/main/scala/com/nawforce/apexlink/types/core/TypeDeclaration.scala
index 56b780faa..b210dc2ca 100644
--- a/jvm/src/main/scala/com/nawforce/apexlink/types/core/TypeDeclaration.scala
+++ b/jvm/src/main/scala/com/nawforce/apexlink/types/core/TypeDeclaration.scala
@@ -38,6 +38,7 @@ import com.nawforce.pkgforce.parsers.{CLASS_NATURE, INTERFACE_NATURE, Nature}
 import com.nawforce.pkgforce.path.{Location, PathLike, PathLocation, UnsafeLocatable}
 
 import java.io.{PrintWriter, StringWriter}
+import java.nio.file.Files
 import scala.collection.immutable.ArraySeq
 import scala.collection.mutable
 
@@ -431,14 +432,7 @@ trait TypeDeclaration extends AbstractTypeDeclaration with Dependent with PreReV
     try {
       validate()
     } catch {
-      case ex: Throwable =>
-        val writer = new StringWriter
-        writer.append("Validation failed")
-        writer.append(": ")
-        ex.printStackTrace(new PrintWriter(writer))
-        OrgInfo.log(
-          Issue(ERROR_CATEGORY, PathLocation(paths.head, Location.empty), writer.toString)
-        )
+      case ex: Throwable => OrgInfo.logException(ex, paths)
     }
   }
 
diff --git a/jvm/src/test/scala/com/nawforce/apexlink/org/OrgInfoTest.scala b/jvm/src/test/scala/com/nawforce/apexlink/org/OrgInfoTest.scala
new file mode 100644
index 000000000..8f7930b94
--- /dev/null
+++ b/jvm/src/test/scala/com/nawforce/apexlink/org/OrgInfoTest.scala
@@ -0,0 +1,88 @@
+/*
+ * Copyright (c) 2024 Certinia Inc. All rights reserved.
+ */
+package com.nawforce.apexlink.org
+
+import com.nawforce.apexlink.TestHelper
+import com.nawforce.pkgforce.diagnostics.LoggerOps.{INFO_LOGGING, NO_LOGGING}
+import com.nawforce.pkgforce.diagnostics.{Logger, LoggerOps}
+import com.nawforce.pkgforce.path.PathLike
+import com.nawforce.runtime.FileSystemHelper
+import org.scalatest.funsuite.AnyFunSuite
+
+import java.io.{File, StringWriter}
+import scala.collection.immutable.ArraySeq
+
+class OrgInfoTest extends AnyFunSuite with TestHelper {
+
+  final class CaptureLogger extends Logger {
+    val writer: StringWriter = new StringWriter()
+
+    override def info(message: String): Unit = {
+      writer.append(s"INFO: $message\n")
+    }
+
+    override def debug(message: String): Unit = {
+      writer.append(s"DEBUG: $message\n")
+    }
+
+    override def trace(message: String): Unit = {
+      writer.append(s"TRACE: $message\n")
+    }
+  }
+
+  test("Log exception without files creates info message") {
+    FileSystemHelper.run(Map()) { root: PathLike =>
+      createOrg(root)
+
+      val captureLogger = new CaptureLogger
+      val oldLogger     = LoggerOps.setLogger(captureLogger)
+      LoggerOps.setLoggingLevel(INFO_LOGGING)
+
+      OrgInfo.logException(new Exception("Hello"), ArraySeq())
+
+      assert(captureLogger.writer.toString.startsWith("INFO: Exception reported against no paths"))
+      assert(captureLogger.writer.toString.contains("INFO: java.lang.Exception: Hello"))
+
+      LoggerOps.setLoggingLevel(NO_LOGGING)
+      LoggerOps.setLogger(oldLogger)
+
+    }
+  }
+
+  test("Log exception captures files") {
+    FileSystemHelper.runTempDir(
+      Map("a.txt" -> "a.txt", "dir1/b.txt" -> "b.txt", "dir1/dir2/c.txt" -> "c.txt")
+    ) { root: PathLike =>
+      createOrg(root)
+
+      val captureLogger = new CaptureLogger
+      val oldLogger     = LoggerOps.setLogger(captureLogger)
+      LoggerOps.setLoggingLevel(INFO_LOGGING)
+
+      try {
+
+        withOrg { _ =>
+          OrgInfo.logException(
+            new Exception("Hello"),
+            ArraySeq(root.join("a.txt"), root.join("dir1/b.txt"), root.join("dir1/dir2/c.txt"))
+          )
+        }
+
+        assert(captureLogger.writer.toString.isEmpty)
+        assert(getMessages().contains("/a.txt: Error: line 1: Validation failed: log directory"))
+        assert(getMessages().contains("java.lang.Exception: Hello"))
+
+        val tmpDir     = getMessages().split("\n").head.split("directory").last.trim
+        val tmpDirPath = new File(tmpDir)
+        assert(tmpDirPath.isDirectory)
+        assert(tmpDirPath.listFiles().map(_.getName).toSet == Set("a.txt", "b.txt", "c.txt"))
+
+      } finally {
+        LoggerOps.setLoggingLevel(NO_LOGGING)
+        LoggerOps.setLogger(oldLogger)
+      }
+    }
+  }
+
+}