diff --git a/CHANGELOG.md b/CHANGELOG.md
index 596d9e4c4..2d04a23d9 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,7 +1,8 @@
 ## {{ UNRELEASED_VERSION }} - [{{ UNRELEASED_DATE }}]({{ UNRELEASED_LINK }})
 
-* Fixed `lando shellenv` failing when shell profile is empty
-* Fixed `lando shellenv` to always include `~/.lando/bin` and include it first
+* Fixed `lando shellenv` so it doesn't fail when `shell` profile is empty
+* Fixed `lando update` so it removes lingering `lando.exe`s in the update bin directory
+* Improved `lando shellenv` so that it always includes `~/.lando/bin` and includes it first
 * Improved messaging on `lando shellenv --add`
 
 ## v3.23.11 - [November 20, 2024](https://github.com/lando/core/releases/tag/v3.23.11)
diff --git a/lib/updates.js b/lib/updates.js
index 8ace61653..0e4a9926a 100644
--- a/lib/updates.js
+++ b/lib/updates.js
@@ -6,6 +6,7 @@ const get = require('lodash/get');
 const getOctokit = require('../utils/get-octokit');
 const os = require('os');
 const path = require('path');
+const remove = require('../utils/remove');
 const semver = require('semver');
 const uniqBy = require('lodash/uniqBy');
 
@@ -249,7 +250,13 @@ module.exports = class UpdateManager {
             // refresh the "symlink"
             require('../utils/link-bin')(this._cli.installPath, dest, {debug: this.debug});
 
-            // is link is not in PATH then attempt to add it
+            // if lando.exe exists on windows in the install path then remove it so the link has primacy
+            // in PATHEXT hierarchy
+            if (process.platform === 'win32' && fs.existsSync(path.join(this._cli.installPath, filename))) {
+              remove(path.join(this._cli.installPath, filename));
+            }
+
+            // if link is not in PATH then attempt to add it
             // @NOTE: feels sufficient to just check for `lando` since it _should_ exist in win and posix
             if (!require('../utils/is-in-path')(path.join(this._cli.installPath, 'lando'))) {
               const binPaths = require('../utils/get-bin-paths')(this._cli);