diff --git a/pkg/cli/cmd.go b/pkg/cli/cmd.go
index 2902035..8b44358 100644
--- a/pkg/cli/cmd.go
+++ b/pkg/cli/cmd.go
@@ -2,6 +2,7 @@ package cli
 
 import (
 	"fmt"
+	"slices"
 	"strings"
 	"time"
 
@@ -51,6 +52,11 @@ var lsCmd = &cobra.Command{
 		//   4lk3 - 4 months ago - Local events and meetups
 		//   43jn - 6 months ago - Mobile photography techniques
 
+		type ConversationLine struct {
+			timeSinceReply time.Duration
+			formatted      string
+		}
+
 		now := time.Now()
 		categories := []string{
 			"recent",
@@ -61,7 +67,7 @@ var lsCmd = &cobra.Command{
 			"last 6 months",
 			"older",
 		}
-		categorized := map[string][]string{}
+		categorized := map[string][]ConversationLine{}
 
 		for _, conversation := range conversations {
 			lastMessage, err := store.LastMessage(&conversation)
@@ -94,7 +100,10 @@ var lsCmd = &cobra.Command{
 				humanTimeElapsedSince(messageAge),
 				conversation.Title,
 			)
-			categorized[category] = append(categorized[category], formatted)
+			categorized[category] = append(
+				categorized[category],
+				ConversationLine{messageAge, formatted},
+			)
 		}
 
 		for _, category := range categories {
@@ -102,9 +111,12 @@ var lsCmd = &cobra.Command{
 			if !ok {
 				continue
 			}
+			slices.SortFunc(conversations, func(a, b ConversationLine) int {
+				return int(a.timeSinceReply - b.timeSinceReply)
+			})
 			fmt.Printf("%s:\n", category)
 			for _, conv := range conversations {
-				fmt.Printf("  %s\n", conv)
+				fmt.Printf("  %s\n", conv.formatted)
 			}
 		}
 	},