diff --git a/crypto/decryptolm.go b/crypto/decryptolm.go
index bd9f1753..ba3c9831 100644
--- a/crypto/decryptolm.go
+++ b/crypto/decryptolm.go
@@ -20,6 +20,7 @@ import (
 	"go.mau.fi/util/exerrors"
 	"go.mau.fi/util/ptr"
 
+	"maunium.net/go/mautrix/crypto/goolm/account"
 	"maunium.net/go/mautrix/event"
 	"maunium.net/go/mautrix/id"
 )
@@ -171,6 +172,7 @@ func (mach *OlmMachine) tryDecryptOlmCiphertext(ctx context.Context, sender id.U
 		return nil, DecryptionFailedForNormalMessage
 	}
 
+	accountBackup, err := mach.account.Internal.Pickle([]byte("tmp"))
 	log.Trace().Msg("Trying to create inbound session")
 	endTimeTrace = mach.timeTrace(ctx, "creating inbound olm session", time.Second)
 	session, err := mach.createInboundSession(ctx, senderKey, ciphertext)
@@ -191,13 +193,20 @@ func (mach *OlmMachine) tryDecryptOlmCiphertext(ctx context.Context, sender id.U
 	plaintext, err = session.Decrypt(ciphertext, olmType)
 	endTimeTrace()
 	if err != nil {
-		go mach.unwedgeDevice(log, sender, senderKey)
 		log.Debug().
 			Hex("ciphertext_hash", ciphertextHash[:]).
 			Hex("ciphertext_hash_repeat", ptr.Ptr(exerrors.Must(olmMessageHash(ciphertext)))[:]).
 			Str("ciphertext", ciphertext).
 			Str("olm_session_description", session.Describe()).
 			Msg("DEBUG: Failed to decrypt prekey olm message with newly created session")
+		err2 := mach.goolmRetryHack(ctx, senderKey, ciphertext, accountBackup)
+		if err2 != nil {
+			log.Debug().Err(err2).Msg("Goolm confirmed decryption failure")
+		} else {
+			log.Warn().Msg("Goolm decryption was successful after libolm failure?")
+		}
+
+		go mach.unwedgeDevice(log, sender, senderKey)
 		return nil, fmt.Errorf("failed to decrypt olm event with session created from prekey message: %w", err)
 	}
 
@@ -214,6 +223,23 @@ func (mach *OlmMachine) tryDecryptOlmCiphertext(ctx context.Context, sender id.U
 	return plaintext, nil
 }
 
+func (mach *OlmMachine) goolmRetryHack(ctx context.Context, senderKey id.SenderKey, ciphertext string, accountBackup []byte) error {
+	acc, err := account.AccountFromPickled(accountBackup, []byte("tmp"))
+	if err != nil {
+		return fmt.Errorf("failed to unpickle olm account: %w", err)
+	}
+	sess, err := acc.NewInboundSessionFrom(&senderKey, ciphertext)
+	if err != nil {
+		return fmt.Errorf("failed to create inbound session: %w", err)
+	}
+	_, err = sess.Decrypt(ciphertext, id.OlmMsgTypePreKey)
+	if err != nil {
+		// This is the expected result if libolm failed
+		return fmt.Errorf("failed to decrypt with new session: %w", err)
+	}
+	return nil
+}
+
 const MaxOlmSessionsPerDevice = 5
 
 func (mach *OlmMachine) tryDecryptOlmCiphertextWithExistingSession(