diff --git a/bridge/bridge.go b/bridge/bridge.go
index e7a39f63..9cfc1450 100644
--- a/bridge/bridge.go
+++ b/bridge/bridge.go
@@ -7,6 +7,7 @@
 package bridge
 
 import (
+	"context"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -219,6 +220,7 @@ type Crypto interface {
 	Stop()
 	Reset(startAfterReset bool)
 	Client() *mautrix.Client
+	ShareKeys(context.Context) error
 }
 
 func (br *Bridge) GenerateRegistration() {
diff --git a/bridge/crypto.go b/bridge/crypto.go
index ccdf7fee..065bc017 100644
--- a/bridge/crypto.go
+++ b/bridge/crypto.go
@@ -436,6 +436,11 @@ func (helper *CryptoHelper) HandleMemberEvent(evt *event.Event) {
 	helper.mach.HandleMemberEvent(0, evt)
 }
 
+// ShareKeys uploads the given number of one-time-keys to the server.
+func (helper *CryptoHelper) ShareKeys(ctx context.Context) error {
+	return helper.mach.ShareKeys(ctx, -1)
+}
+
 type cryptoSyncer struct {
 	*crypto.OlmMachine
 }
diff --git a/crypto/machine.go b/crypto/machine.go
index 98da7686..2c9b63c9 100644
--- a/crypto/machine.go
+++ b/crypto/machine.go
@@ -622,8 +622,8 @@ func (mach *OlmMachine) ShareKeys(ctx context.Context, currentOTKCount int) erro
 	start := time.Now()
 	mach.otkUploadLock.Lock()
 	defer mach.otkUploadLock.Unlock()
-	if mach.lastOTKUpload.Add(1 * time.Minute).After(start) {
-		log.Debug().Msg("Checking OTK count from server due to suspiciously close share keys requests")
+	if mach.lastOTKUpload.Add(1*time.Minute).After(start) || currentOTKCount < 0 {
+		log.Debug().Msg("Checking OTK count from server due to suspiciously close share keys requests or negative OTK count")
 		resp, err := mach.Client.UploadKeys(&mautrix.ReqUploadKeys{})
 		if err != nil {
 			return fmt.Errorf("failed to check current OTK counts: %w", err)