diff --git a/src/cli/commands/update.rs b/src/cli/commands/update.rs
index 785219b..e532342 100644
--- a/src/cli/commands/update.rs
+++ b/src/cli/commands/update.rs
@@ -7,6 +7,7 @@ use crate::{
   error::{MultiError, PakkerError},
   model::{Config, LockFile, UpdateStrategy},
   ui_utils::{prompt_select, prompt_typo_suggestion, prompt_yes_no},
+  utils::FlexVer,
 };
 
 pub async fn execute(
@@ -141,6 +142,15 @@ pub async fn execute(
       && !updated_project.files.is_empty()
       && let Some(old_file) = lockfile.projects[idx].files.first()
     {
+      // Sort files by FlexVer if that strategy is set
+      if old_project.update_strategy == UpdateStrategy::FlexVer {
+        updated_project.files.sort_by(|a, b| {
+          // Use FlexVer for comparison - b.cmp(a) gives descending order
+          // (newest first)
+          FlexVer(&b.file_name).cmp(&FlexVer(&a.file_name))
+        });
+      }
+
       // Clone data needed for comparisons to avoid borrow issues
       let new_file_id = updated_project.files.first().unwrap().id.clone();
       let new_file_name =