diff --git a/Analyser/Static/Enterprise/StaticAnalyser.cpp b/Analyser/Static/Enterprise/StaticAnalyser.cpp
index 4965b0496..75a19b74d 100644
--- a/Analyser/Static/Enterprise/StaticAnalyser.cpp
+++ b/Analyser/Static/Enterprise/StaticAnalyser.cpp
@@ -11,6 +11,21 @@
 
 #include "../../../Storage/Disk/Parsers/FAT.hpp"
 
+#include <algorithm>
+
+namespace {
+
+bool insensitive_equal(const std::string &lhs, const std::string &rhs) {
+	return std::equal(
+		lhs.begin(), lhs.end(),
+		rhs.begin(), rhs.end(),
+		[] (char l, char r) {
+			return tolower(l) == tolower(r);
+	});
+}
+
+}
+
 Analyser::Static::TargetList Analyser::Static::Enterprise::GetTargets(const Media &media, const std::string &, TargetPlatform::IntType) {
 	// This analyser can comprehend disks only.
 	if(media.disks.empty()) return {};
@@ -26,8 +41,38 @@ Analyser::Static::TargetList Analyser::Static::Enterprise::GetTargets(const Medi
 
 	// Inspect any supplied disks.
 	if(!media.disks.empty()) {
-		auto volume = Storage::Disk::FAT::GetVolume(media.disks.front());
+		// DOS will be needed.
 		target->dos = Target::DOS::EXDOS;
+
+		// Grab the volume information, which includes the root directory.
+		auto volume = Storage::Disk::FAT::GetVolume(media.disks.front());
+		if(volume) {
+			// If there's an EXDOS.INI then this disk should be able to boot itself.
+			// If not but if there's only one .COM or .BAS, automatically load that.
+			// Failing that, issue a :DIR and give the user a clue as to how to load.
+			const Storage::Disk::FAT::File *selected_file = nullptr;
+			bool has_exdos_ini = false;
+			bool did_pick_file = false;
+			for(const auto &file: (*volume).root_directory) {
+				if(insensitive_equal(file.name, "EXDOS   ") && insensitive_equal(file.extension, "INI")) {
+					has_exdos_ini = true;
+					break;
+				}
+
+				if(insensitive_equal(file.extension, "com") || insensitive_equal(file.extension, "bas")) {
+					did_pick_file = !selected_file;
+					selected_file = &file;
+				}
+			}
+
+			if(!has_exdos_ini) {
+				if(did_pick_file) {
+					target->loading_command = std::string("run \"") + selected_file->name + "." + selected_file->extension + "\"";
+				} else {
+					target->loading_command = ":dir";
+				}
+			}
+		}
 	}
 
 	targets.push_back(std::unique_ptr<Analyser::Static::Target>(target));