diff --git a/php/ext/google/protobuf/php-upb.c b/php/ext/google/protobuf/php-upb.c
index 602509a64a..7ccb946143 100644
--- a/php/ext/google/protobuf/php-upb.c
+++ b/php/ext/google/protobuf/php-upb.c
@@ -6143,7 +6143,6 @@ upb_EnumReservedRange* _upb_EnumReservedRanges_New(
         google_protobuf_EnumDescriptorProto_EnumReservedRange_start(protos[i]);
     const int32_t end =
         google_protobuf_EnumDescriptorProto_EnumReservedRange_end(protos[i]);
-    const int32_t max = kUpb_MaxFieldNumber + 1;
 
     // A full validation would also check that each range is disjoint, and that
     // none of the fields overlap with the extension ranges, but we are just
@@ -6151,7 +6150,7 @@ upb_EnumReservedRange* _upb_EnumReservedRanges_New(
 
     // Note: Not a typo! Unlike extension ranges and message reserved ranges,
     // the end value of an enum reserved range is *inclusive*!
-    if (start < 1 || end < start || end > max) {
+    if (end < start) {
       symtab_errf(ctx, "Reserved range (%d, %d) is invalid, enum=%s\n",
                            (int)start, (int)end, upb_EnumDef_FullName(e));
     }
@@ -8184,7 +8183,7 @@ static void create_fielddef(
     CHK_OOM(
         upb_strtable_insert(&oneof->ntof, name.data, name.size, v, ctx->arena));
   } else {
-    if (f->proto3_optional_) {
+    if (f->proto3_optional_ && !is_extension) {
       symtab_errf(ctx, "field with proto3_optional was not in a oneof (%s)",
                   f->full_name);
     }
diff --git a/protobuf_deps.bzl b/protobuf_deps.bzl
index 6aee8b76dd..0949ef370a 100644
--- a/protobuf_deps.bzl
+++ b/protobuf_deps.bzl
@@ -117,6 +117,6 @@ def protobuf_deps():
         _github_archive(
             name = "upb",
             repo = "https://github.com/protocolbuffers/upb",
-            commit = "969f6fdb88e94ced87953e53716893c68ec7b1ce",
-            sha256 = "6754b7f95c92f69a832a82931aea40d066cc689dbc1eb3348b84c1ed95285296",
+            commit = "20b542a767139732548f7b8cf28c4c928cdcb07b",
+            sha256 = "c77158955326f9e9a0cf8481c118b8ad5c34df99e5db3af27f3d1662d8bedef7",
         )
diff --git a/ruby/ext/google/protobuf_c/ruby-upb.c b/ruby/ext/google/protobuf_c/ruby-upb.c
index 85b1d0f2ff..3d3c35be93 100755
--- a/ruby/ext/google/protobuf_c/ruby-upb.c
+++ b/ruby/ext/google/protobuf_c/ruby-upb.c
@@ -5814,7 +5814,6 @@ upb_EnumReservedRange* _upb_EnumReservedRanges_New(
         google_protobuf_EnumDescriptorProto_EnumReservedRange_start(protos[i]);
     const int32_t end =
         google_protobuf_EnumDescriptorProto_EnumReservedRange_end(protos[i]);
-    const int32_t max = kUpb_MaxFieldNumber + 1;
 
     // A full validation would also check that each range is disjoint, and that
     // none of the fields overlap with the extension ranges, but we are just
@@ -5822,7 +5821,7 @@ upb_EnumReservedRange* _upb_EnumReservedRanges_New(
 
     // Note: Not a typo! Unlike extension ranges and message reserved ranges,
     // the end value of an enum reserved range is *inclusive*!
-    if (start < 1 || end < start || end > max) {
+    if (end < start) {
       symtab_errf(ctx, "Reserved range (%d, %d) is invalid, enum=%s\n",
                            (int)start, (int)end, upb_EnumDef_FullName(e));
     }
@@ -7855,7 +7854,7 @@ static void create_fielddef(
     CHK_OOM(
         upb_strtable_insert(&oneof->ntof, name.data, name.size, v, ctx->arena));
   } else {
-    if (f->proto3_optional_) {
+    if (f->proto3_optional_ && !is_extension) {
       symtab_errf(ctx, "field with proto3_optional was not in a oneof (%s)",
                   f->full_name);
     }