From 066ab1bc32687228bddd4dbae872d64f621101c0 Mon Sep 17 00:00:00 2001
From: Linus Rath <139418639+rathlinus@users.noreply.github.com>
Date: Mon, 30 Mar 2026 19:15:02 +0200
Subject: [PATCH] debug: add diagnostic logging to 3DES S/MIME decrypt path

Log legacy key import success/failure, CMS algorithm OIDs (content
encryption + key transport), legacy key availability during decrypt
attempts, and detailed error messages from both RSA-OAEP and
RSAES-PKCS1-v1_5 decrypt paths.
---
 components/email/email-viewer.tsx |  7 ++++++-
 lib/smime/pkcs12-import.ts        |  8 ++++++--
 lib/smime/smime-decrypt.ts        | 19 +++++++++++++++++--
 3 files changed, 29 insertions(+), 5 deletions(-)

diff --git a/components/email/email-viewer.tsx b/components/email/email-viewer.tsx
index 04bf8c68..68af0db0 100644
--- a/components/email/email-viewer.tsx
+++ b/components/email/email-viewer.tsx
@@ -1546,7 +1546,12 @@ export function EmailViewer({
         if (detection.type === 'enveloped-data') {
           // Encrypted message
             const { keyRecords, unlockedDecryptionKeys, unlockedLegacyDecryptionKeys } = smimeStore;
-            smimeDebug('[S/MIME] decrypt attempt:', { keyRecordCount: keyRecords.length, unlockedKeyCount: unlockedDecryptionKeys.size, keyRecordIds: keyRecords.map(k => k.id) });
+            smimeDebug('[S/MIME] decrypt attempt:', {
+              keyRecordCount: keyRecords.length,
+              unlockedKeyCount: unlockedDecryptionKeys.size,
+              legacyKeyCount: unlockedLegacyDecryptionKeys.size,
+              keyRecordIds: keyRecords.map(k => k.id),
+            });
 
           // Short-circuit: no keys imported at all
           if (keyRecords.length === 0) {
diff --git a/lib/smime/pkcs12-import.ts b/lib/smime/pkcs12-import.ts
index 3be315bc..a503e85d 100644
--- a/lib/smime/pkcs12-import.ts
+++ b/lib/smime/pkcs12-import.ts
@@ -298,8 +298,12 @@ export async function unlockPrivateKey(
         false,
         ['decrypt'],
       );
-    } catch {
-      // webcrypto-liner may not be available or key format unsupported
+      console.debug('[S/MIME] legacy RSAES-PKCS1-v1_5 key imported successfully:', {
+        algorithm: legacyDecryptionKey.algorithm,
+        usages: legacyDecryptionKey.usages,
+      });
+    } catch (err) {
+      console.warn('[S/MIME] legacy RSAES-PKCS1-v1_5 key import failed:', err);
     }
   }
 
diff --git a/lib/smime/smime-decrypt.ts b/lib/smime/smime-decrypt.ts
index 3a641687..3e3b3300 100644
--- a/lib/smime/smime-decrypt.ts
+++ b/lib/smime/smime-decrypt.ts
@@ -42,6 +42,18 @@ export async function smimeDecrypt(input: DecryptionInput): Promise<DecryptionRe
   const contentInfo = parseContentInfo(cmsBytes);
   const envelopedData = extractEnvelopedData(contentInfo);
 
+  // Log CMS algorithm details for diagnostics
+  const contentEncOid = envelopedData.encryptedContentInfo?.contentEncryptionAlgorithm?.algorithmId;
+  const recipientAlgs = envelopedData.recipientInfos?.map((ri) =>
+    // eslint-disable-next-line @typescript-eslint/no-explicit-any
+    (ri as any).value?.keyEncryptionAlgorithm?.algorithmId as string | undefined,
+  );
+  console.debug('[S/MIME] CMS algorithms:', {
+    contentEncryption: contentEncOid,
+    keyTransport: recipientAlgs,
+    legacyKeysAvailable: legacyUnlockedKeys?.size ?? 0,
+  });
+
   // Find matching key records
   const matchedRecords = findMatchingKeyRecords(envelopedData, keyRecords);
 
@@ -75,9 +87,11 @@ export async function smimeDecrypt(input: DecryptionInput): Promise<DecryptionRe
         mimeBytes: new Uint8Array(decrypted),
         keyRecordId: keyRecord.id,
       };
-    } catch {
+    } catch (oaepError) {
       // RSA-OAEP key didn't work, try legacy RSAES-PKCS1-v1_5 key
+      console.debug('[S/MIME] RSA-OAEP decrypt failed:', oaepError instanceof Error ? oaepError.message : oaepError);
       const legacyKey = legacyUnlockedKeys?.get(keyRecord.id);
+      console.debug('[S/MIME] legacy key available:', !!legacyKey, legacyKey ? { algorithm: (legacyKey as CryptoKey).algorithm } : undefined);
       if (legacyKey) {
         try {
           const decrypted = await decryptWithKey(envelopedData, recipientIndex, legacyKey, keyRecord);
@@ -85,8 +99,9 @@ export async function smimeDecrypt(input: DecryptionInput): Promise<DecryptionRe
             mimeBytes: new Uint8Array(decrypted),
             keyRecordId: keyRecord.id,
           };
-        } catch {
+        } catch (legacyError) {
           // Legacy key also didn't work, try the next record
+          console.debug('[S/MIME] RSAES-PKCS1-v1_5 decrypt also failed:', legacyError instanceof Error ? legacyError.message : legacyError);
         }
       }
       continue;