diff --git a/telegram/utils.go b/telegram/utils.go
index 430b507..a1de641 100644
--- a/telegram/utils.go
+++ b/telegram/utils.go
@@ -3032,10 +3032,41 @@ func (c *Client) sendMessagesReverse(chatID int64, messages []*client.Message, p
 				from = sChatId
 			}
 
+			body := c.formatMessage(0, 0, false, !isMUC, message)
+
+			// OMEMO encrypt hook - same rules as SendMessageToGateway's (see
+			// its doc comment): personal-chat pseudo-JIDs only, gated on
+			// the per-chat active flag, once per logical (historical)
+			// message. Real content must never go out in the clear if
+			// OMEMO is active but a session can't be established or
+			// encryption fails - gateway.OMEMOSendFailedBody is sent
+			// instead. This is the !history command's send path
+			// (sendMessagesReverse's plain branch) - easy to miss since it
+			// bypasses SendMessageToGateway entirely.
+			var envelope *e2ee.Envelope
+			if !isMUC && body != "" {
+				if backend, ok := gateway.E2EE.Backend(); ok {
+					owner := e2ee.OwnedPeer(c.Session.Login, gateway.CHATJID(chatID, false))
+					if active, _ := backend.Enabled(owner); active {
+						peer := e2ee.PeerID(c.jid)
+						if err := c.ensureOMEMOSession(backend, owner, peer); err != nil {
+							log.Error(errors.Wrap(err, "Failed to establish OMEMO session"))
+							body = gateway.OMEMOSendFailedBody
+						} else if env, err := backend.Encrypt(owner, []e2ee.PeerID{peer}, []byte(body)); err != nil {
+							log.Error(errors.Wrap(err, "Failed to encrypt OMEMO message"))
+							body = gateway.OMEMOSendFailedBody
+						} else {
+							envelope = &env
+						}
+					}
+				}
+			}
+
 			for _, to := range plainTos {
 				gateway.SendMessage(to, from, c.xmpp,
-					gateway.SMBody(c.formatMessage(0, 0, false, !isMUC, message)), gateway.SMId(sId),
+					gateway.SMBody(body), gateway.SMId(sId),
 					gateway.SMReply(reply), gateway.SMIsGroupchat(isMUC), gateway.SMOriginalFrom(originalFrom),
+					gateway.SMOMEMOEnvelope(envelope),
 				)
 			}
 		} else {