diff --git a/app/src/main/java/io/timelimit/android/logic/crypto/CryptDataHandler.kt b/app/src/main/java/io/timelimit/android/logic/crypto/CryptDataHandler.kt
index a6e597f..7850b2f 100644
--- a/app/src/main/java/io/timelimit/android/logic/crypto/CryptDataHandler.kt
+++ b/app/src/main/java/io/timelimit/android/logic/crypto/CryptDataHandler.kt
@@ -116,7 +116,9 @@ object CryptDataHandler {
         database.cryptContainer().updateMetadata(updatedMetadata)
 
         if (updatedMetadata.status == CryptContainerMetadata.ProcessingStatus.MissingKey && header != null) {
-            if (database.cryptContainerKeyRequest().byCryptContainerId(currentItem.cryptContainerId) == null) {
+            val existingRequest = database.cryptContainerKeyRequest().byCryptContainerId(currentItem.cryptContainerId)
+
+            if (existingRequest == null || existingRequest.requestTimeCryptContainerGeneration < header.generation) {
                 val signingKey = DeviceSigningKey.getPublicAndPrivateKeySync(database)!!.let { Curve25519.getPrivateKey(it) }
                 val requestKeyPair = Curve25519.generateKeyPair()
                 val sequenceNumber = database.config().getNextSigningSequenceNumberAndIncrementIt()
@@ -143,6 +145,8 @@ object CryptDataHandler {
                     ), database
                 )
 
+                if (existingRequest != null) database.cryptContainerKeyRequest().delete(existingRequest)
+
                 database.cryptContainerKeyRequest().insert(
                     CryptContainerPendingKeyRequest(
                         cryptContainerId = currentItem.cryptContainerId,