diff --git a/bin/bot/src/discord/handler/brain/functions/moderation.rs b/bin/bot/src/discord/handler/brain/functions/moderation.rs
index a0feb78..d58e7c9 100644
--- a/bin/bot/src/discord/handler/brain/functions/moderation.rs
+++ b/bin/bot/src/discord/handler/brain/functions/moderation.rs
@@ -1,5 +1,5 @@
 use serde_json::json;
-use serenity::prelude::Context;
+use serenity::{model::Timestamp, prelude::Context};
 use synixe_meta::discord::{channel::LOG, GUILD};
 use time::{Duration, OffsetDateTime};
 
@@ -68,9 +68,11 @@ impl BrainFunction for Timeout {
                 error!("failed to get member: {}", id);
                 continue;
             };
-            if member.communication_disabled_until.is_some() {
-                info!("user already timed out: {}", member.user.id);
-                continue;
+            if let Some(until) = member.communication_disabled_until {
+                if until > Timestamp::now() {
+                    info!("user already timed out: {}", member.user.id);
+                    continue;
+                }
             }
             info!("timing out user: {}", member.user.id);
             if let Err(e) = member