diff --git a/server/fleet/errors.go b/server/fleet/errors.go
index ed6bf27187..c14da53e11 100644
--- a/server/fleet/errors.go
+++ b/server/fleet/errors.go
@@ -538,11 +538,11 @@ func (e OrbitError) Error() string {
 const (
 	// Scripts
 	RunScriptInvalidTypeErrMsg             = "File type not supported. Only .sh (Bash) and .ps1 (PowerShell) file types are allowed."
-	RunScriptHostOfflineErrMsg             = "Script can’t run on offline host."
-	RunScriptHostNotFoundErrMsg            = "Host doesn’t exist. Make sure you provide a valid hostname, UUID, osquery host ID, or node key."
-	RunScriptForbiddenErrMsg               = "You don’t have the right permissions in Fleet to run the script."
+	RunScriptHostOfflineErrMsg             = "Script can't run on offline host."
+	RunScriptHostNotFoundErrMsg            = "Host doesn't exist. Make sure you provide a valid hostname, UUID, osquery host ID, or node key."
+	RunScriptForbiddenErrMsg               = "You don't have the right permissions in Fleet to run the script."
 	RunScriptAlreadyRunningErrMsg          = "A script is already running on this host. Please wait about 5 minutes to let it finish."
-	RunScriptHostTimeoutErrMsg             = "Fleet didn’t hear back from the host in under 5 minutes (timeout for live scripts). Fleet doesn’t know if the script ran because it didn’t receive the result. Please try again."
+	RunScriptHostTimeoutErrMsg             = "Fleet didn't hear back from the host in under 5 minutes (timeout for live scripts). Fleet doesn't know if the script ran because it didn't receive the result. Please try again."
 	RunScriptScriptsDisabledGloballyErrMsg = "Running scripts is disabled in organization settings."
 	RunScriptDisabledErrMsg                = "Scripts are disabled for this host. To run scripts, deploy the fleetd agent with scripts enabled."
 	RunScriptsOrbitDisabledErrMsg          = "Couldn't run script. To run a script, deploy the fleetd agent with --enable-scripts."
@@ -550,6 +550,7 @@ const (
 	RunScriptAsyncScriptEnqueuedErrMsg     = "Script is running or will run when the host comes online."
 	RunScripSavedMaxLenErrMsg              = "Script is too large. It's limited to 500,000 characters (approximately 10,000 lines)."
 	RunScripUnsavedMaxLenErrMsg            = "Script is too large. It's limited to 10,000 characters (approximately 125 lines)."
+	RunScriptGatewayTimeoutErrMsg          = "Gateway timeout. Fleet didn't hear back from the host and doesn't know if the script ran. Please make sure your load balancer timeout isn't shorter than the Fleet server timeout."
 
 	// End user authentication
 	EndUserAuthDEPWebURLConfiguredErrMsg = `End user authentication can't be configured when the configured automatic enrollment (DEP) profile specifies a configuration_web_url.` // #nosec G101
diff --git a/server/service/client_scripts.go b/server/service/client_scripts.go
index 18285013fd..373b3b1ebd 100644
--- a/server/service/client_scripts.go
+++ b/server/service/client_scripts.go
@@ -57,6 +57,11 @@ func (c *Client) runHostScript(verb, path string, hostID uint, scriptContents []
 			return nil, errors.New(fleet.RunScriptScriptsDisabledGloballyErrMsg)
 		}
 		return nil, errors.New(fleet.RunScriptForbiddenErrMsg)
+	// It's possible we get a GatewayTimeout error message from nginx or another
+	// proxy server, so we want to return a more helpful error message in that
+	// case.
+	case http.StatusGatewayTimeout:
+		return nil, errors.New(fleet.RunScriptGatewayTimeoutErrMsg)
 	case http.StatusPaymentRequired:
 		if teamID > 0 {
 			return nil, errors.New("Team id parameter requires Fleet Premium license.")