diff --git a/ui/desktop/app/components/session/tabs/index.js b/ui/desktop/app/components/session/tabs/index.js
index 7ef617fbc..c1334a728 100644
--- a/ui/desktop/app/components/session/tabs/index.js
+++ b/ui/desktop/app/components/session/tabs/index.js
@@ -66,17 +66,17 @@ export default class SessionTerminalTabsComponent extends Component {
     this.id = uuidv4();
     this.#setupTerminal(fitAddon, xterm, termContainer);
 
-    const { isWindows } = await this.ipc.invoke('checkOS');
+    const isSSHCommandAvailable = await this.ipc.invoke('checkCommand', 'ssh');
     const { model } = this.args;
 
     const { proxy_address, proxy_port, started_desktop_client, target } = model;
 
-    // Only send the command on certain scenarios:
+    // Only send the command in certain scenarios:
     // 1. Only for SSH targets
-    // 2. Don't connect for windows as most users won't have an openSSH client installed
-    // 3. Don't connect if the session wasn't initiated in the desktop client
+    // 2. Don't connect if the session wasn't initiated in the desktop client
     //    which means we won't have proxy information
-    if (target?.isSSH && started_desktop_client && !isWindows) {
+    // 3. Only connect if the user has an SSH client available in their path
+    if (target?.isSSH && started_desktop_client && isSSHCommandAvailable) {
       // Send an SSH command immediately
       window.terminal.send(
         `ssh ${proxy_address} -p ${proxy_port} -o NoHostAuthenticationForLocalhost=yes\r`,
diff --git a/ui/desktop/electron-app/package.json b/ui/desktop/electron-app/package.json
index 34575e6c0..d62f7daed 100644
--- a/ui/desktop/electron-app/package.json
+++ b/ui/desktop/electron-app/package.json
@@ -30,7 +30,8 @@
     "semver": "^7.5.3",
     "shell-env": "^3.0.1",
     "shell-quote": "^1.7.3",
-    "tree-kill": "^1.2.2"
+    "tree-kill": "^1.2.2",
+    "which": "^4.0.0"
   },
   "devDependencies": {
     "@electron-forge/cli": "^6.1.1",
diff --git a/ui/desktop/electron-app/src/ipc/handlers.js b/ui/desktop/electron-app/src/ipc/handlers.js
index 68a729be2..943db257b 100644
--- a/ui/desktop/electron-app/src/ipc/handlers.js
+++ b/ui/desktop/electron-app/src/ipc/handlers.js
@@ -13,6 +13,7 @@ const sanitizer = require('../utils/sanitizer.js');
 const { isLinux, isMac, isWindows } = require('../helpers/platform.js');
 const os = require('node:os');
 const pty = require('node-pty');
+const which = require('which');
 
 /**
  * Returns the current runtime clusterUrl, which is used by the main thread to
@@ -112,13 +113,9 @@ handle('toggleFullscreenWindow', () => {
 handle('closeWindow', () => app.quit());
 
 /**
- * Return an object containing helper fields for determining what OS we're running on
+ * Return the location of where a user's binary for a command is. If it isn't found, return null.
  */
-handle('checkOS', () => ({
-  isLinux: isLinux(),
-  isMac: isMac(),
-  isWindows: isWindows(),
-}));
+handle('checkCommand', async (command) => which(command, { nothrow: true }));
 
 /**
  * Handler to help create terminal windows. We don't use the helper `handle` method
diff --git a/ui/desktop/electron-app/yarn.lock b/ui/desktop/electron-app/yarn.lock
index e14c6cdb5..9b7f3cf01 100644
--- a/ui/desktop/electron-app/yarn.lock
+++ b/ui/desktop/electron-app/yarn.lock
@@ -1962,6 +1962,11 @@ isexe@^2.0.0:
   resolved "https://registry.yarnpkg.com/isexe/-/isexe-2.0.0.tgz#e8fbf374dc556ff8947a10dcb0572d633f2cfa10"
   integrity sha1-6PvzdNxVb/iUehDcsFctYz8s+hA=
 
+isexe@^3.1.1:
+  version "3.1.1"
+  resolved "https://registry.yarnpkg.com/isexe/-/isexe-3.1.1.tgz#4a407e2bd78ddfb14bea0c27c6f7072dde775f0d"
+  integrity sha512-LpB/54B+/2J5hqQ7imZHfdU31OlgQqx7ZicVlkm9kzg9/w8GKLEcFfJl/t7DCEDueOyBAD6zCCwTO6Fzs0NoEQ==
+
 jackspeak@^2.0.3:
   version "2.3.3"
   resolved "https://registry.yarnpkg.com/jackspeak/-/jackspeak-2.3.3.tgz#95e4cbcc03b3eb357bf6bcce14a903fb3d1151e1"
@@ -3513,6 +3518,13 @@ which@^2.0.1, which@^2.0.2:
   dependencies:
     isexe "^2.0.0"
 
+which@^4.0.0:
+  version "4.0.0"
+  resolved "https://registry.yarnpkg.com/which/-/which-4.0.0.tgz#cd60b5e74503a3fbcfbf6cd6b4138a8bae644c1a"
+  integrity sha512-GlaYyEb07DPxYCKhKzplCWBJtvxZcZMrL+4UkrTSJHHPyZU4mYYTv3qaOe77H7EODLSSopAUFAc6W8U4yqvscg==
+  dependencies:
+    isexe "^3.1.1"
+
 wide-align@^1.1.5:
   version "1.1.5"
   resolved "https://registry.yarnpkg.com/wide-align/-/wide-align-1.1.5.tgz#df1d4c206854369ecf3c9a4898f1b23fbd9d15d3"