diff --git a/src/main/kotlin/moe/kageru/kagebot/extensions/ArrowExtensions.kt b/src/main/kotlin/moe/kageru/kagebot/extensions/ArrowExtensions.kt
index 24f4853..ce3ea53 100644
--- a/src/main/kotlin/moe/kageru/kagebot/extensions/ArrowExtensions.kt
+++ b/src/main/kotlin/moe/kageru/kagebot/extensions/ArrowExtensions.kt
@@ -1,7 +1,11 @@
 package moe.kageru.kagebot.extensions
 
 import arrow.core.Either
+import arrow.core.Option
+import arrow.core.Tuple3
 import arrow.core.getOrElse
+import arrow.optics.pFirst
+import arrow.optics.pSecond
 
 fun <L, R> Either<L, R>.on(op: (R) -> Unit): Either<L, R> {
     this.map { op(it) }
@@ -9,3 +13,11 @@ fun <L, R> Either<L, R>.on(op: (R) -> Unit): Either<L, R> {
 }
 
 fun <T> Either<*, T>.unwrap(): T = getOrElse { error("Attempted to unwrap Either.left") }
+
+fun <A, B, C, R> Tuple3<A, B, C>.mapSecond(op: (B) -> Option<R>): Option<Tuple3<A, R, C>> {
+    return op(this.b).map { Tuple3.pSecond<A, B, C, R>().set(this, it) }
+}
+
+fun <A, B, C, R> Tuple3<A, B, C>.mapFirst(op: (A) -> Option<R>): Option<Tuple3<R, B, C>> {
+    return op(this.a).map { Tuple3.pFirst<A, B, C, R>().set(this, it) }
+}
diff --git a/src/main/kotlin/moe/kageru/kagebot/features/TimeoutFeature.kt b/src/main/kotlin/moe/kageru/kagebot/features/TimeoutFeature.kt
index 90cfabb..238c9a8 100644
--- a/src/main/kotlin/moe/kageru/kagebot/features/TimeoutFeature.kt
+++ b/src/main/kotlin/moe/kageru/kagebot/features/TimeoutFeature.kt
@@ -1,8 +1,11 @@
 package moe.kageru.kagebot.features
 
-import arrow.core.*
+import arrow.core.Either
+import arrow.core.Tuple3
+import arrow.core.extensions.either.monad.flatMap
 import arrow.core.extensions.list.monad.map
 import arrow.core.extensions.listk.functorFilter.filter
+import arrow.core.toOption
 import arrow.syntax.collections.destructured
 import com.fasterxml.jackson.annotation.JsonProperty
 import moe.kageru.kagebot.Log
@@ -11,10 +14,7 @@ import moe.kageru.kagebot.Util.findRole
 import moe.kageru.kagebot.Util.findUser
 import moe.kageru.kagebot.config.Config
 import moe.kageru.kagebot.config.LocalizationSpec
-import moe.kageru.kagebot.extensions.memberById
-import moe.kageru.kagebot.extensions.on
-import moe.kageru.kagebot.extensions.roles
-import moe.kageru.kagebot.extensions.unwrap
+import moe.kageru.kagebot.extensions.*
 import moe.kageru.kagebot.persistence.Dao
 import org.javacord.api.entity.permission.Role
 import org.javacord.api.entity.user.User
@@ -32,12 +32,9 @@ class TimeoutFeature(@JsonProperty("role") role: String) : MessageFeature {
                 { Tuple3(args[1], args[2], args.getOrNull(3)) },
                 { "Error: expected “<command> <user> <time> [<reason>]”. If the name contains spaces, please use the user ID instead." }
             ).flatMap {
-                Tuple3(
-                    findUser(it.a).orNull()
-                        ?: return@flatMap "Error: User ${it.a} not found, consider using the user ID".left(),
-                    it.b.toLongOrNull() ?: return@flatMap "Error: malformed time “${it.b}”".left(),
-                    it.c
-                ).right()
+                it.mapFirst(::findUser).toEither { "Error: User ${it.a} not found, consider using the user ID" }
+            }.flatMap {
+                it.mapSecond { time -> time.toLongOrNull().toOption() }.toEither { "Error: malformed time “${it.b}”" }
             }.on { (user, time, _) ->
                 applyTimeout(user, time)
             }.fold(