diff --git a/.github/workflows/dev-release.yml b/.github/workflows/dev-release.yml
index 6b6327176..8eef1dc3c 100644
--- a/.github/workflows/dev-release.yml
+++ b/.github/workflows/dev-release.yml
@@ -120,7 +120,6 @@ jobs:
         alias:
           - dev
           - ${{ github.sha }}
-
     needs:
       - build-release-binary-alias
       - build-release-binary-branch
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 37ceb089f..e3105458a 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -129,7 +129,6 @@ jobs:
           - edge
           - ${{ github.event.release.prerelease == false && 'stable' || 'prerelease' }}
           - ${{ github.ref_name }}
-
     needs:
       - build-release-binary-alias
       - build-release-binary-tag
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 74f787494..298946008 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,11 @@
 ## {{ UNRELEASED_VERSION }} - [{{ UNRELEASED_DATE }}]({{ UNRELEASED_LINK }})
 
+* 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`
+* Improved messaging on `lando update` for `@lando/cli`
+
 ## v3.23.11 - [November 20, 2024](https://github.com/lando/core/releases/tag/v3.23.11)
 
 * This release has no new content and is just to test the new modular release flow
diff --git a/lib/checksums.txt b/lib/checksums.txt
deleted file mode 100644
index e69de29bb..000000000
diff --git a/lib/updates.js b/lib/updates.js
index 8ace61653..1739e5246 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 +250,16 @@ 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
+            // set a good default update messag
+            task.title = `Updated @lando/cli to ${version}`;
+
+            // if lando.exe exists on windows in the install path then remove it so the link has primacy
+            // in PATHEXT hierarchy
+            if (process.platform === 'win32' && fs.existsSync(path.join(this._cli.installPath, filename))) {
+              remove(path.join(this._cli.installPath, filename));
+            }
+
+            // if link is not in PATH then attempt to add it
             // @NOTE: feels sufficient to just check for `lando` since it _should_ exist in win and posix
             if (!require('../utils/is-in-path')(path.join(this._cli.installPath, 'lando'))) {
               const binPaths = require('../utils/get-bin-paths')(this._cli);
@@ -269,6 +279,7 @@ module.exports = class UpdateManager {
                 const rcFile = require('../utils/get-shell-profile')();
                 require('../utils/update-shell-profile')(rcFile, shellEnv);
                 this.debug('added %o to %o', shellEnv, rcFile);
+                task.title `${task.title}. Start a new terminal session to use the updated ${color.bold(`lando`)}`;
 
               // otherwis i guess do something else?
               // @TODO: throw a warning?
@@ -276,7 +287,6 @@ module.exports = class UpdateManager {
             }
 
             // finish
-            task.title = `Updated @lando/cli to ${version}`;
             resolve(data);
           });
           // handle errors
diff --git a/tasks/shellenv.js b/tasks/shellenv.js
index f2812e08c..91f0caf99 100644
--- a/tasks/shellenv.js
+++ b/tasks/shellenv.js
@@ -62,7 +62,7 @@ module.exports = lando => {
           console.log();
           console.log(color.bold(binPaths.join(os.EOL)));
           console.log();
-          console.log(`Open a new shell to load the changes!`);
+          console.log(`Start a new terminal session to use ${color.bold(`lando`)}`);
           return;
 
         // otherwise update the shell profile
@@ -72,7 +72,7 @@ module.exports = lando => {
           console.log();
           console.log(color.bold(shellEnv.map(line => line[0]).join(os.EOL)));
           console.log();
-          console.log(`Open a new shell or run ${color.bold(`source ${options.add}`)} to load the changes`);
+          console.log(`Start a new terminal session or run ${color.bold(`eval "$(lando shellenv)"`)} to use ${color.bold(`lando`)}`);
         } else {
           console.log(`Looks like ${color.green(options.add)} is already ready to go!`);
         }
diff --git a/utils/get-bin-paths.js b/utils/get-bin-paths.js
index 9ea6865ba..db09c27c3 100644
--- a/utils/get-bin-paths.js
+++ b/utils/get-bin-paths.js
@@ -3,8 +3,8 @@
 const fs = require('fs');
 const path = require('path');
 
-module.exports = ({entrypoint, file, installPath}) => {
-  return [entrypoint, file, installPath]
+module.exports = ({installPath}) => {
+  return [installPath]
     .filter(p => typeof p === 'string' && p !== '' && fs.existsSync(p))
     .map(p => !fs.lstatSync(p).isDirectory() ? path.dirname(p) : p)
     .filter(p => !process.env.PATH.split(path.delimiter).includes(p))
diff --git a/utils/update-shell-profile.js b/utils/update-shell-profile.js
index eddc9a989..239e1866b 100644
--- a/utils/update-shell-profile.js
+++ b/utils/update-shell-profile.js
@@ -18,8 +18,11 @@ module.exports = (file, updates = []) => {
     const content = read(file);
     // split into lines
     const lines = content.split('\n');
+    // get penulimatimate
+    const penny = Math.max(lines.length - 2, 0);
+
     // if we end up with second to last line that is empty then pop
-    if (lines[lines.length - 2].trim() === '') lines.pop();
+    if (penny > 0 && lines[lines.length - 2].trim() === '') lines.pop();
 
     // loops through the updates and add/update as needed
     for (const [update, search] of updates) {