diff --git a/cli/app/list.go b/cli/app/list.go
index be0753e7..443a5422 100644
--- a/cli/app/list.go
+++ b/cli/app/list.go
@@ -173,7 +173,7 @@ Use "--status/-S" flag to query all servers for the live deployment status.`,
 							stats.LatestCount++
 						}
 					} else {
-						newUpdates = internal.ReverseStringList(newUpdates)
+						newUpdates = internal.SortVersionsDesc(newUpdates)
 						appStats.Upgrade = strings.Join(newUpdates, "\n")
 						stats.UpgradeCount++
 					}
diff --git a/cli/app/rollback.go b/cli/app/rollback.go
index 3535a393..09ca206d 100644
--- a/cli/app/rollback.go
+++ b/cli/app/rollback.go
@@ -167,7 +167,7 @@ beforehand.`,
 
 				prompt := &survey.Select{
 					Message: msg,
-					Options: internal.ReverseStringList(availableDowngrades),
+					Options: internal.SortVersionsDesc(availableDowngrades),
 				}
 
 				if err := survey.AskOne(prompt, &chosenDowngrade); err != nil {
diff --git a/cli/app/upgrade.go b/cli/app/upgrade.go
index 7e5624cf..bee884ef 100644
--- a/cli/app/upgrade.go
+++ b/cli/app/upgrade.go
@@ -159,7 +159,7 @@ beforehand.`,
 
 				prompt := &survey.Select{
 					Message: msg,
-					Options: internal.ReverseStringList(availableUpgrades),
+					Options: internal.SortVersionsDesc(availableUpgrades),
 				}
 
 				if err := survey.AskOne(prompt, &chosenUpgrade); err != nil {
diff --git a/cli/internal/deploy.go b/cli/internal/deploy.go
index 5485b91f..79a7fac9 100644
--- a/cli/internal/deploy.go
+++ b/cli/internal/deploy.go
@@ -3,12 +3,14 @@ package internal
 import (
 	"fmt"
 	"os"
+	"sort"
 	"strings"
 
 	appPkg "coopcloud.tech/abra/pkg/app"
 	"coopcloud.tech/abra/pkg/config"
 	"coopcloud.tech/abra/pkg/formatter"
 	"coopcloud.tech/abra/pkg/log"
+	"coopcloud.tech/tagcmp"
 	"github.com/AlecAivazis/survey/v2"
 	"github.com/charmbracelet/lipgloss"
 	dockerClient "github.com/docker/docker/client"
@@ -274,3 +276,22 @@ func PostCmds(cl *dockerClient.Client, app appPkg.App, commands string) error {
 	}
 	return nil
 }
+
+// SortVersionsDesc sorts versions in descending order.
+func SortVersionsDesc(versions []string) []string {
+	var tags []tagcmp.Tag
+
+	for _, v := range versions {
+		parsed, _ := tagcmp.Parse(v) // skips unsupported tags
+		tags = append(tags, parsed)
+	}
+
+	sort.Sort(tagcmp.ByTagDesc(tags))
+
+	var desc []string
+	for _, t := range tags {
+		desc = append(desc, t.String())
+	}
+
+	return desc
+}
diff --git a/cli/internal/list.go b/cli/internal/list.go
deleted file mode 100644
index d2a89527..00000000
--- a/cli/internal/list.go
+++ /dev/null
@@ -1,10 +0,0 @@
-package internal
-
-// ReverseStringList reverses a list of a strings. Roll on Go generics.
-func ReverseStringList(strings []string) []string {
-	for i, j := 0, len(strings)-1; i < j; i, j = i+1, j-1 {
-		strings[i], strings[j] = strings[j], strings[i]
-	}
-
-	return strings
-}