diff --git a/src/crash_handler.zig b/src/crash_handler.zig
index 8d7323e20b..963d0080b2 100644
--- a/src/crash_handler.zig
+++ b/src/crash_handler.zig
@@ -308,6 +308,7 @@ pub fn handleRootError(err: anyerror, error_return_trace: ?*std.builtin.StackTra
 
         error.InvalidArgument,
         error.@"Invalid Bunfig",
+        error.InstallFailed,
         => if (!show_trace) Global.exit(1),
 
         error.SyntaxError => {
diff --git a/src/install/install.zig b/src/install/install.zig
index 5e0c2e0225..ded44f50d9 100644
--- a/src/install/install.zig
+++ b/src/install/install.zig
@@ -7389,15 +7389,35 @@ pub const PackageManager = struct {
     }
 
     pub inline fn update(ctx: Command.Context) !void {
-        try updatePackageJSONAndInstall(ctx, .update, .update);
+        try updatePackageJSONAndInstallCatchError(ctx, .update, .update);
     }
 
     pub inline fn add(ctx: Command.Context) !void {
-        try updatePackageJSONAndInstall(ctx, .add, .add);
+        try updatePackageJSONAndInstallCatchError(ctx, .add, .add);
     }
 
     pub inline fn remove(ctx: Command.Context) !void {
-        try updatePackageJSONAndInstall(ctx, .remove, .remove);
+        try updatePackageJSONAndInstallCatchError(ctx, .remove, .remove);
+    }
+
+    pub fn updatePackageJSONAndInstallCatchError(
+        ctx: Command.Context,
+        comptime op: Lockfile.Package.Diff.Op,
+        comptime subcommand: Subcommand,
+    ) !void {
+        updatePackageJSONAndInstall(ctx, op, subcommand) catch |err| {
+            switch (err) {
+                error.InstallFailed,
+                error.InvalidPackageJSON,
+                => {
+                    const log = &bun.CLI.Cli.log_;
+                    log.printForLogLevel(bun.Output.errorWriter()) catch {};
+                    bun.Global.exit(1);
+                    return;
+                },
+                else => return err,
+            }
+        };
     }
 
     pub inline fn link(ctx: Command.Context) !void {
diff --git a/src/install/lockfile.zig b/src/install/lockfile.zig
index dcf1aa336d..a5ca2fc54a 100644
--- a/src/install/lockfile.zig
+++ b/src/install/lockfile.zig
@@ -3799,10 +3799,6 @@ pub const Package = extern struct {
         }
 
         pub fn insert(self: *WorkspaceMap, key: string, value: Entry) !void {
-            if (comptime Environment.allow_assert) {
-                assert(!strings.containsChar(key, std.fs.path.sep_windows));
-            }
-
             if (comptime Environment.isDebug) {
                 if (!bun.sys.exists(key)) {
                     Output.debugWarn("WorkspaceMap.insert: key {s} does not exist", .{key});