diff --git a/FlowCrypt/src/main/java/com/flowcrypt/email/security/SecurityUtils.kt b/FlowCrypt/src/main/java/com/flowcrypt/email/security/SecurityUtils.kt
index 8426396e37..7e8b453821 100644
--- a/FlowCrypt/src/main/java/com/flowcrypt/email/security/SecurityUtils.kt
+++ b/FlowCrypt/src/main/java/com/flowcrypt/email/security/SecurityUtils.kt
@@ -13,6 +13,7 @@ import com.flowcrypt.email.database.FlowCryptRoomDatabase
 import com.flowcrypt.email.database.entity.AccountEntity
 import com.flowcrypt.email.extensions.org.bouncycastle.openpgp.toPgpKeyDetails
 import com.flowcrypt.email.security.model.PgpKeyDetails
+import com.flowcrypt.email.security.pgp.PgpDecrypt
 import com.flowcrypt.email.security.pgp.PgpKey
 import com.flowcrypt.email.security.pgp.PgpPwd
 import com.flowcrypt.email.util.exception.DifferentPassPhrasesException
@@ -161,5 +162,13 @@ class SecurityUtils {
     fun generateRandomUUID(): String {
       return String(Hex.encodeHex(DigestUtils.sha1(UUID.randomUUID().toString())))
     }
+
+    /**
+     * Check if the file extension fits the encrypted pattern.
+     * If yes - it can mean the file is encrypted
+     */
+    fun isEncryptedData(fileName: String?): Boolean {
+      return PgpDecrypt.DETECT_SEPARATE_ENCRYPTED_ATTACHMENTS_PATTERN.find(fileName ?: "") != null
+    }
   }
 }
diff --git a/FlowCrypt/src/main/java/com/flowcrypt/email/service/attachment/AttachmentDownloadManagerService.kt b/FlowCrypt/src/main/java/com/flowcrypt/email/service/attachment/AttachmentDownloadManagerService.kt
index 358ceef11d..b4dfd8e2d2 100644
--- a/FlowCrypt/src/main/java/com/flowcrypt/email/service/attachment/AttachmentDownloadManagerService.kt
+++ b/FlowCrypt/src/main/java/com/flowcrypt/email/service/attachment/AttachmentDownloadManagerService.kt
@@ -37,6 +37,7 @@ import com.flowcrypt.email.database.entity.AccountEntity
 import com.flowcrypt.email.extensions.kotlin.toHex
 import com.flowcrypt.email.jetpack.viewmodel.AccountViewModel
 import com.flowcrypt.email.security.KeysStorageImpl
+import com.flowcrypt.email.security.SecurityUtils
 import com.flowcrypt.email.security.pgp.PgpDecrypt
 import com.flowcrypt.email.util.FileAndDirectoryUtils
 import com.flowcrypt.email.util.GeneralUtil
@@ -653,8 +654,7 @@ class AttachmentDownloadManagerService : Service() {
         throw NullPointerException("Error. The file is missing")
       }
 
-      val regex = PgpDecrypt.DETECT_SEPARATE_ENCRYPTED_ATTACHMENTS_PATTERN
-      if (regex.find(att.name ?: "") == null) {
+      if (!SecurityUtils.isEncryptedData(att.name)) {
         return file
       }
 
diff --git a/FlowCrypt/src/main/java/com/flowcrypt/email/service/attachment/AttachmentNotificationManager.kt b/FlowCrypt/src/main/java/com/flowcrypt/email/service/attachment/AttachmentNotificationManager.kt
index 4e07dc6763..1f48c70d99 100644
--- a/FlowCrypt/src/main/java/com/flowcrypt/email/service/attachment/AttachmentNotificationManager.kt
+++ b/FlowCrypt/src/main/java/com/flowcrypt/email/service/attachment/AttachmentNotificationManager.kt
@@ -130,22 +130,22 @@ class AttachmentNotificationManager(context: Context) : CustomNotificationManage
   fun errorHappened(context: Context, attInfo: AttachmentInfo, e: Exception) {
     val builder = genDefBuilder(context, attInfo)
 
-    val bitText = StringBuilder()
+    val bigText = StringBuilder()
     val contentText = StringBuilder()
     when {
       TextUtils.isEmpty(e.message) -> {
         contentText.append(context.getString(R.string.error_occurred_please_try_again))
-        bitText.append(e.javaClass.simpleName)
+        bigText.append(e.javaClass.simpleName)
       }
 
       e.cause != null -> {
         contentText.append(e.cause?.message ?: "")
-        bitText.append(e.javaClass.simpleName + ": " + e.message)
+        bigText.append(e.javaClass.simpleName + ": " + e.message)
       }
 
       else -> {
         contentText.append(e.message)
-        bitText.append(e.javaClass.simpleName + ": " + e.message)
+        bigText.append(e.javaClass.simpleName + ": " + e.message)
       }
     }
 
@@ -159,7 +159,7 @@ class AttachmentNotificationManager(context: Context) : CustomNotificationManage
             R.plurals.please_provide_passphrase_for_following_keys,
             1
           ) + "\n" + GeneralUtil.doSectionsInText(" ", it, 4) + "\n\n"
-          bitText.insert(0, additionalText)
+          bigText.insert(0, additionalText)
         }
       }
     }
@@ -175,8 +175,8 @@ class AttachmentNotificationManager(context: Context) : CustomNotificationManage
       .setGroup(GROUP_NAME_ATTACHMENTS)
       .setGroupAlertBehavior(NotificationCompat.GROUP_ALERT_CHILDREN)
 
-    if (bitText.isNotEmpty()) {
-      builder.setStyle(NotificationCompat.BigTextStyle().bigText(bitText))
+    if (bigText.isNotEmpty()) {
+      builder.setStyle(NotificationCompat.BigTextStyle().bigText(bigText))
     }
 
     notificationManagerCompat.notify(attInfo.id, attInfo.uid.toInt(), builder.build())
diff --git a/FlowCrypt/src/main/java/com/flowcrypt/email/ui/activity/fragment/MessageDetailsFragment.kt b/FlowCrypt/src/main/java/com/flowcrypt/email/ui/activity/fragment/MessageDetailsFragment.kt
index e567907768..ec6c65bb90 100644
--- a/FlowCrypt/src/main/java/com/flowcrypt/email/ui/activity/fragment/MessageDetailsFragment.kt
+++ b/FlowCrypt/src/main/java/com/flowcrypt/email/ui/activity/fragment/MessageDetailsFragment.kt
@@ -72,6 +72,7 @@ import com.flowcrypt.email.jetpack.viewmodel.factory.MsgDetailsViewModelFactory
 import com.flowcrypt.email.model.MessageEncryptionType
 import com.flowcrypt.email.model.MessageType
 import com.flowcrypt.email.model.PgpContact
+import com.flowcrypt.email.security.SecurityUtils
 import com.flowcrypt.email.service.attachment.AttachmentDownloadManagerService
 import com.flowcrypt.email.ui.activity.CreateMessageActivity
 import com.flowcrypt.email.ui.activity.ImportPrivateKeyActivity
@@ -129,6 +130,21 @@ class MessageDetailsFragment : BaseFragment(), ProgressBehaviour, View.OnClickLi
       override fun onDownloadClick(attachmentInfo: AttachmentInfo) {
         lastClickedAtt = attachmentInfo
         lastClickedAtt?.orderNumber = GeneralUtil.genAttOrderId(requireContext())
+
+        if (SecurityUtils.isEncryptedData(attachmentInfo.name)) {
+          for (block in msgInfo?.msgBlocks ?: emptyList()) {
+            if (block.type == MsgBlock.Type.DECRYPT_ERROR) {
+              val decryptErrorMsgBlock = block as? DecryptErrorMsgBlock ?: continue
+              val decryptErrorDetails = decryptErrorMsgBlock.error?.details ?: continue
+              if (decryptErrorDetails.type == DecryptErrorDetails.Type.NEED_PASSPHRASE) {
+                val fingerprints = decryptErrorMsgBlock.error.longIds?.needPassphrase ?: continue
+                showNeedPassphraseDialog(fingerprints)
+                return
+              }
+            }
+          }
+        }
+
         if (Build.VERSION.SDK_INT >= Build.VERSION_CODES.Q ||
           ContextCompat.checkSelfPermission(
             requireContext(),