diff --git a/tools/cli/cli-context.cpp b/tools/cli/cli-context.cpp
index 74d60eb19d..0de8f69025 100644
--- a/tools/cli/cli-context.cpp
+++ b/tools/cli/cli-context.cpp
@@ -153,9 +153,19 @@ bool cli_context::init() {
 
     if (use_external_server) {
         spinner.reset();
-        if (!list_and_ask_models()) {
+        try {
+            if (!list_and_ask_models()) {
+                return false;
+            }
+        } catch (const json::parse_error & e) {
+            ui::show_error(e.what());
+            ui::show_message("This might be caused by an incorrect server-base endpoint URL");
+            return false;
+        } catch (const std::exception & e) {
+            ui::show_error(e.what());
             return false;
         }
+
         // restore the spinner for the next step
         spinner.emplace("Waiting for server...");
     }