diff --git a/cl/compile.go b/cl/compile.go
index bc073c23de..efc048c80d 100644
--- a/cl/compile.go
+++ b/cl/compile.go
@@ -853,8 +853,21 @@ func (p *context) compileInstrOrValue(b llssa.Builder, iv instrOrValue, asValue
 			b.DeferStackDrain()
 		}
 	case *ssa.BinOp:
-		x := p.compileValue(b, v.X)
-		y := p.compileValue(b, v.Y)
+		if isUntypedNilConst(v.X) && isUntypedNilConst(v.Y) {
+			switch v.Op {
+			case token.EQL:
+				ret = p.prog.BoolVal(true)
+				break
+			case token.NEQ:
+				ret = p.prog.BoolVal(false)
+				break
+			}
+			if !ret.IsNil() {
+				break
+			}
+		}
+		x := p.compileValueAs(b, v.X, v.Y.Type())
+		y := p.compileValueAs(b, v.Y, v.X.Type())
 		ret = b.BinOp(v.Op, x, y)
 	case *ssa.UnOp:
 		if v.Op == token.MUL {
@@ -891,10 +904,18 @@ func (p *context) compileInstrOrValue(b llssa.Builder, iv instrOrValue, asValue
 		}
 	case *ssa.ChangeType:
 		t := v.Type()
+		if isUntypedNilConst(v.X) {
+			ret = p.nilOf(t)
+			break
+		}
 		x := p.compileValue(b, v.X)
 		ret = b.ChangeType(p.type_(t, llssa.InGo), x)
 	case *ssa.Convert:
 		t := v.Type()
+		if isUntypedNilConst(v.X) {
+			ret = p.nilOf(t)
+			break
+		}
 		x := p.compileValue(b, v.X)
 		ret = b.Convert(p.type_(t, llssa.InGo), x)
 	case *ssa.FieldAddr:
@@ -967,6 +988,10 @@ func (p *context) compileInstrOrValue(b llssa.Builder, iv instrOrValue, asValue
 			}
 		}
 		t := p.type_(v.Type(), llssa.InGo)
+		if isUntypedNilConst(v.X) {
+			ret = p.prog.Nil(t)
+			break
+		}
 		if unop, ok := v.X.(*ssa.UnOp); ok && unop.Op == token.MUL {
 			if vt := p.type_(unop.Type(), llssa.InGo); vt.RawType() != nil {
 				if p.isLargeNonPointerValue(vt) {
@@ -1047,6 +1072,26 @@ func (p *context) compileInstrOrValue(b llssa.Builder, iv instrOrValue, asValue
 	return ret
 }
 
+func isUntypedNilConst(v ssa.Value) bool {
+	c, ok := v.(*ssa.Const)
+	if !ok || c.Value != nil {
+		return false
+	}
+	basic, ok := c.Type().Underlying().(*types.Basic)
+	return ok && basic.Kind() == types.UntypedNil
+}
+
+func (p *context) nilOf(typ types.Type) llssa.Expr {
+	return p.prog.Nil(p.type_(typ, llssa.InGo))
+}
+
+func (p *context) compileValueAs(b llssa.Builder, v ssa.Value, typ types.Type) llssa.Expr {
+	if isUntypedNilConst(v) {
+		return p.nilOf(typ)
+	}
+	return p.compileValue(b, v)
+}
+
 func (p *context) assertNilDerefBase(b llssa.Builder, addr ssa.Value) {
 	if field, ok := addr.(*ssa.FieldAddr); ok {
 		base := p.compileValue(b, field.X)
diff --git a/test/go/switch_nil_test.go b/test/go/switch_nil_test.go
new file mode 100644
index 0000000000..f825aee370
--- /dev/null
+++ b/test/go/switch_nil_test.go
@@ -0,0 +1,115 @@
+package gotest
+
+import "testing"
+
+func TestSwitchNilCases(t *testing.T) {
+	switch f := func() {}; f {
+	case nil:
+		t.Fatal("non-nil func matched nil")
+	default:
+	}
+
+	var nilFunc func()
+	switch nilFunc {
+	case nil:
+	default:
+		t.Fatal("nil func did not match nil")
+	}
+
+	switch m := make(map[int]int); m {
+	case nil:
+		t.Fatal("non-nil map matched nil")
+	default:
+	}
+
+	var nilMap map[int]int
+	switch nilMap {
+	case nil:
+	default:
+		t.Fatal("nil map did not match nil")
+	}
+
+	switch s := make([]int, 1); s {
+	case nil:
+		t.Fatal("non-nil slice matched nil")
+	default:
+	}
+
+	var nilSlice []int
+	switch nilSlice {
+	case nil:
+	default:
+		t.Fatal("nil slice did not match nil")
+	}
+
+	switch c1, c2 := make(chan int), make(chan int); c1 {
+	case nil:
+		t.Fatal("non-nil channel matched nil")
+	case c2:
+		t.Fatal("channel matched a different channel")
+	case c1:
+	default:
+		t.Fatal("channel did not match itself")
+	}
+
+	switch (*int)(nil) {
+	case nil:
+	case any(nil):
+		t.Fatal("typed nil pointer matched nil interface")
+	default:
+		t.Fatal("typed nil pointer did not match nil")
+	}
+}
+
+func TestGenericSwitchNilCases(t *testing.T) {
+	checkGenericNilSwitch[int](t)
+	checkGenericNilSwitch[string](t)
+}
+
+func checkGenericNilSwitch[T any](t *testing.T) {
+	switch []T(nil) {
+	case nil:
+	default:
+		t.Fatal("nil generic slice did not match nil")
+	}
+	if []T(nil) != nil {
+		t.Fatal("nil generic slice compared non-nil")
+	}
+
+	switch make([]T, 1) {
+	case nil:
+		t.Fatal("non-nil generic slice matched nil")
+	default:
+	}
+
+	switch (func() T)(nil) {
+	case nil:
+	default:
+		t.Fatal("nil generic func did not match nil")
+	}
+	if (func() T)(nil) != nil {
+		t.Fatal("nil generic func compared non-nil")
+	}
+
+	var zero T
+	switch func() T { return zero } {
+	case nil:
+		t.Fatal("non-nil generic func matched nil")
+	default:
+	}
+
+	switch (map[int]T)(nil) {
+	case nil:
+	default:
+		t.Fatal("nil generic map did not match nil")
+	}
+	if (map[int]T)(nil) != nil {
+		t.Fatal("nil generic map compared non-nil")
+	}
+
+	switch make(map[int]T) {
+	case nil:
+		t.Fatal("non-nil generic map matched nil")
+	default:
+	}
+}
diff --git a/test/goroot/xfail.yaml b/test/goroot/xfail.yaml
index a5a66d10b4..ae8e5a0787 100644
--- a/test/goroot/xfail.yaml
+++ b/test/goroot/xfail.yaml
@@ -1818,10 +1818,6 @@ xfails:
     directive: run
     case: unsafebuiltins.go
     reason: current main goroot run failure on darwin/arm64
-  - platform: darwin/arm64
-    directive: run
-    case: switch.go
-    reason: current main goroot run failure on darwin/arm64
   - platform: darwin/arm64
     directive: run
     case: zerodivide.go
@@ -3660,10 +3656,6 @@ xfails:
     directive: run
     case: fixedbugs/issue47928.go
     reason: current main goroot run failure on darwin/arm64
-  - platform: darwin/arm64
-    directive: run
-    case: fixedbugs/issue53635.go
-    reason: current main goroot run failure on darwin/arm64
   - platform: darwin/arm64
     directive: run
     case: fixedbugs/issue60601.go
@@ -3858,10 +3850,6 @@ xfails:
     directive: run
     case: fixedbugs/issue47928.go
     reason: current main goroot run failure on linux/amd64
-  - platform: linux/amd64
-    directive: run
-    case: fixedbugs/issue53635.go
-    reason: current main goroot run failure on linux/amd64
   - platform: linux/amd64
     directive: run
     case: fixedbugs/issue60601.go