diff --git a/tcd.py b/tcd.py
index 7b857e1..f0d603c 100644
--- a/tcd.py
+++ b/tcd.py
@@ -188,11 +188,23 @@ def main():
         print("NOTICE: No new entries found to transcribe.")
         sys.exit(0)
 
-    eprint("Transcribing: {}".format(", ".join(files_to_transcribe)))
+    eprint(
+        "Transcribing {} files: {}".format(
+            str(len(files_to_transcribe)), ", ".join(files_to_transcribe)
+        )
+    )
     for index, f in enumerate(files_to_transcribe):
-        transcribe_with_timestamp(os.path.join(tcd_path, f))
-        if index != len(files):
-            print("\n\n")
+        eprint(
+            "Transcribing file {}: {} ({})".format(
+                index + 1, f, converttcdfilename(f)
+            )
+        )
+        try:
+            transcribe_with_timestamp(os.path.join(tcd_path, f))
+            if index != len(files):
+                print("\n\n")
+        except:
+            eprint("Transcription failed!")
 
     writelast(files_to_transcribe[-1])
     sys.exit(0)