diff --git a/ipa-core/src/cli/crypto.rs b/ipa-core/src/cli/crypto.rs
index 84871776a..8428f477d 100644
--- a/ipa-core/src/cli/crypto.rs
+++ b/ipa-core/src/cli/crypto.rs
@@ -129,8 +129,10 @@ async fn build_hpke_registry(
 }
 
 struct DecryptedReports {
+    filename: PathBuf,
     reader: BufReader<File>,
     key_registry: KeyRegistry<PrivateKeyOnly>,
+    iter_index: usize,
 }
 
 impl DecryptedReports {
@@ -139,8 +141,10 @@ impl DecryptedReports {
             .unwrap_or_else(|e| panic!("unable to open file {filename:?}. {e}"));
         let reader = BufReader::new(file);
         Self {
+            filename: filename.to_path_buf(),
             reader,
             key_registry,
+            iter_index: 0,
         }
     }
 }
@@ -151,11 +155,22 @@ impl Iterator for DecryptedReports {
     fn next(&mut self) -> Option<Self::Item> {
         let mut line = String::new();
         if self.reader.read_line(&mut line).unwrap() > 0 {
+            self.iter_index += 1;
             let encrypted_report_bytes = hex::decode(line.trim()).unwrap();
             let enc_report =
                 EncryptedOprfReport::from_bytes(encrypted_report_bytes.as_slice()).unwrap();
             let dec_report = enc_report.decrypt(&self.key_registry);
-            Some(dec_report)
+            match dec_report {
+                Ok(dec_report) => Some(Ok(dec_report)),
+                Err(e) => {
+                    eprintln!(
+                        "Decryption failed: File: {0}. Record: {1}. Error: {e}.",
+                        self.filename.display(),
+                        self.iter_index
+                    );
+                    Some(Err(e))
+                }
+            }
         } else {
             None
         }
@@ -180,10 +195,8 @@ pub async fn decrypt_and_reconstruct(args: DecryptArgs) -> Result<(), BoxError>
             .create_new(true)
             .open(args.output_file)?,
     );
-    let mut first_error = Ok(());
-    for (idx, (dec_report1, (dec_report2, dec_report3))) in decrypted_reports1
-        .zip(decrypted_reports2.zip(decrypted_reports3))
-        .enumerate()
+    for (dec_report1, (dec_report2, dec_report3)) in
+        decrypted_reports1.zip(decrypted_reports2.zip(decrypted_reports3))
     {
         match (dec_report1, dec_report2, dec_report3) {
             (Ok(dec_report1), Ok(dec_report2), Ok(dec_report3)) => {
@@ -236,32 +249,9 @@ pub async fn decrypt_and_reconstruct(args: DecryptArgs) -> Result<(), BoxError>
                     trigger_value,
                 )?;
             }
-            // error handling in case decryption failed
-            (Err(e1), _, _) => {
-                writeln!(writer, "Decryption failed Record: {idx} Reason:{e1}",)?;
-                eprintln!("Decryption failed Record: {idx} Reason:{e1}");
-                if first_error.is_ok() {
-                    first_error = Err(e1);
-                }
-            }
-            (Ok(_), Err(e2), _) => {
-                writeln!(writer, "Decryption failed Record: {idx} Reason:{e2}",)?;
-                eprintln!("Decryption failed Record: {idx} Reason:{e2}");
-                if first_error.is_ok() {
-                    first_error = Err(e2);
-                }
-            }
-            (Ok(_), Ok(_), Err(e3)) => {
-                writeln!(writer, "Decryption failed Record: {idx} Reason:{e3}",)?;
-                eprintln!("Decryption failed Record: {idx} Reason:{e3}");
-                if first_error.is_ok() {
-                    first_error = Err(e3);
-                }
-            }
+            (_, _, _) => {}
         }
     }
-
-    first_error.unwrap();
     Ok(())
 }