diff --git a/sync3/extensions/todevice.go b/sync3/extensions/todevice.go
index 951177b3..430c3da5 100644
--- a/sync3/extensions/todevice.go
+++ b/sync3/extensions/todevice.go
@@ -65,6 +65,30 @@ func (r *ToDeviceRequest) ProcessInitial(ctx context.Context, res *Response, ext
 		r.Limit = 100 // default to 100
 	}
 	l := logger.With().Str("user", extCtx.UserID).Str("device", extCtx.DeviceID).Logger()
+
+	mapMu.Lock()
+	lastSentPos, exists := deviceIDToSinceDebugOnly[extCtx.DeviceID]
+	internal.Logf(ctx, "to_device", "since=%v limit=%v last_sent=%v", r.Since, r.Limit, lastSentPos)
+	isFirstRequest := !exists
+	mapMu.Unlock()
+
+	// If this is the first time we've seen this device ID since starting up, ignore the client-provided 'since'
+	// value. This is done to protect against dropped postgres sequences. Consider:
+	//   - 5 to-device messages arrive for Alice
+	//   - Alice requests all messages, gets them and acks them so since=5, and the nextval() sequence is 6.
+	//   - the server admin drops the DB and starts over again. The DB sequence starts back at 1.
+	//   - 2 to-device messages arrive for Alice
+	//   - Alice requests messages from since=5. No messages are returned as the 2 new messages have a lower sequence number.
+	//   - Even worse, those 2 messages are deleted because sending since=5 ACKNOWLEDGES all messages <=5.
+	// By ignoring the first `since` on startup, we effectively force the client into sending since=0. In this scenario,
+	// it will then A) not delete anything as since=0 acknowledges nothing, B) return the 2 to-device events.
+	//
+	// The cost to this is that it is possible to send duplicate to-device events if the server restarts before the client
+	// has time to send the ACK to the server. This isn't fatal as clients do suppress duplicate to-device events.
+	if isFirstRequest {
+		r.Since = ""
+	}
+
 	var from int64
 	var err error
 	if r.Since != "" {
@@ -82,10 +106,7 @@ func (r *ToDeviceRequest) ProcessInitial(ctx context.Context, res *Response, ext
 			internal.GetSentryHubFromContextOrDefault(ctx).CaptureException(err)
 		}
 	}
-	mapMu.Lock()
-	lastSentPos := deviceIDToSinceDebugOnly[extCtx.DeviceID]
-	internal.Logf(ctx, "to_device", "since=%v limit=%v last_sent=%v", r.Since, r.Limit, lastSentPos)
-	mapMu.Unlock()
+
 	if from < lastSentPos {
 		// we told the client about a newer position, but yet they are using an older position, yell loudly
 		l.Warn().Int64("last_sent", lastSentPos).Int64("recv", from).Bool("initial", extCtx.IsInitial).Msg(