diff --git a/internal/css_printer/css_printer.go b/internal/css_printer/css_printer.go
index e42947ba0a..4c1a184794 100644
--- a/internal/css_printer/css_printer.go
+++ b/internal/css_printer/css_printer.go
@@ -444,7 +444,14 @@ func (p *printer) printMediaQuery(query css_ast.MediaQuery, flags mqFlags) {
 		p.printIdent(q.Type, identNormal, 0)
 		if q.AndOrNull.Data != nil {
 			p.print(" and ")
-			p.printMediaQuery(q.AndOrNull, 0)
+			// An "or" condition after a media type must be wrapped in parentheses
+			// to preserve grouping, e.g. "screen and ((a) or (b))" must keep the
+			// outer parentheses since "screen and (a) or (b)" is invalid CSS.
+			andFlags := mqFlags(0)
+			if binary, ok := q.AndOrNull.Data.(*css_ast.MQBinary); ok && binary.Op == css_ast.MQBinaryOpOr {
+				andFlags = mqNeedsParens
+			}
+			p.printMediaQuery(q.AndOrNull, andFlags)
 		}
 
 	case *css_ast.MQNot:
diff --git a/internal/css_printer/css_printer_test.go b/internal/css_printer/css_printer_test.go
index f02dbf7dd3..c0403d74e3 100644
--- a/internal/css_printer/css_printer_test.go
+++ b/internal/css_printer/css_printer_test.go
@@ -370,6 +370,11 @@ func TestAtMedia(t *testing.T) {
 	expectPrintedMinify(t, "@media not ( (a) or (b) ) {div{color:red}}", "@media not ((a)or (b)){div{color:red}}")
 	expectPrintedMinify(t, "@media not ( (a) and (b) ) {div{color:red}}", "@media not ((a)and (b)){div{color:red}}")
 
+	// Nested "or" inside a media type must preserve outer parentheses (https://github.com/evanw/esbuild/issues/4395)
+	expectPrintedMinify(t, "@media only screen and ((min-width: 10px) or (min-height: 10px)) {div{color:red}}", "@media only screen and ((min-width:10px)or (min-height:10px)){div{color:red}}")
+	expectPrintedMinify(t, "@media screen and ((a) or (b)) {div{color:red}}", "@media screen and ((a)or (b)){div{color:red}}")
+	expectPrinted(t, "@media only screen and ((min-width: 10px) or (min-height: 10px)) { div { color: red } }", "@media only screen and ((min-width: 10px) or (min-height: 10px)) {\n  div {\n    color: red;\n  }\n}\n")
+
 	expectPrintedMinify(t, "@media (width < 2px) {div{color:red}}", "@media(width<2px){div{color:red}}")
 	expectPrintedMinify(t, "@media (1px < width) {div{color:red}}", "@media(1px<width){div{color:red}}")
 	expectPrintedMinify(t, "@media (1px < width < 2px) {div{color:red}}", "@media(1px<width<2px){div{color:red}}")