diff --git a/spec/css/functions/special.hrx b/spec/css/functions/special.hrx
index fd59cb3ae..96ba0108b 100644
--- a/spec/css/functions/special.hrx
+++ b/spec/css/functions/special.hrx
@@ -25,3 +25,187 @@ a {b: -a-calc(#{0})}
 a {
   b: -a-calc(0);
 }
+
+<===>
+================================================================================
+<===> comment/calc/after_open_paren/loud/input.scss
+a {b: -a-calc(/**/ c)}
+
+<===> comment/calc/after_open_paren/loud/output.css
+a {
+  b: -a-calc(/**/ c);
+}
+
+<===>
+================================================================================
+<===> comment/calc/after_open_paren/silent/input.scss
+a {
+  b: -a-calc(//
+    c);
+}
+
+<===> comment/calc/after_open_paren/silent/output.css
+a {
+  b: -a-calc( c);
+}
+
+<===>
+================================================================================
+<===> comment/calc/before_close_paren/loud/input.scss
+a {b: -a-calc(c /**/)}
+
+<===> comment/calc/before_close_paren/loud/output.css
+a {
+  b: -a-calc(c /**/);
+}
+
+<===>
+================================================================================
+<===> comment/calc/before_close_paren/silent/input.scss
+a {
+  b: -a-calc(c //
+    );
+}
+
+<===> comment/calc/before_close_paren/silent/output.css
+a {
+  b: -a-calc(c  );
+}
+
+<===>
+================================================================================
+<===> comment/element/after_open_paren/loud/input.scss
+a {b: element(/**/ c)}
+
+<===> comment/element/after_open_paren/loud/output.css
+a {
+  b: element(/**/ c);
+}
+
+<===>
+================================================================================
+<===> comment/element/after_open_paren/silent/input.scss
+a {
+  b: element(//
+    c);
+}
+
+<===> comment/element/after_open_paren/silent/output.css
+a {
+  b: element( c);
+}
+
+<===>
+================================================================================
+<===> comment/element/before_close_paren/loud/input.scss
+a {b: element(c /**/)}
+
+<===> comment/element/before_close_paren/loud/output.css
+a {
+  b: element(c /**/);
+}
+
+<===>
+================================================================================
+<===> comment/element/before_close_paren/silent/input.scss
+a {
+  b: element(c //
+    );
+}
+
+<===> comment/element/before_close_paren/silent/output.css
+a {
+  b: element(c  );
+}
+
+<===>
+================================================================================
+<===> comment/expression/after_open_paren/loud/input.scss
+a {b: expression(/**/ c)}
+
+<===> comment/expression/after_open_paren/loud/output.css
+a {
+  b: expression(/**/ c);
+}
+
+<===>
+================================================================================
+<===> comment/expression/after_open_paren/silent/input.scss
+a {
+  b: expression(//
+    c);
+}
+
+<===> comment/expression/after_open_paren/silent/output.css
+a {
+  b: expression( c);
+}
+
+<===>
+================================================================================
+<===> comment/expression/before_close_paren/loud/input.scss
+a {b: expression(c /**/)}
+
+<===> comment/expression/before_close_paren/loud/output.css
+a {
+  b: expression(c /**/);
+}
+
+<===>
+================================================================================
+<===> comment/expression/before_close_paren/silent/input.scss
+a {
+  b: expression(c //
+    );
+}
+
+<===> comment/expression/before_close_paren/silent/output.css
+a {
+  b: expression(c  );
+}
+
+<===>
+================================================================================
+<===> comment/progid/after_open_paren/loud/input.scss
+a {b: progid:c(/**/ d)}
+
+<===> comment/progid/after_open_paren/loud/output.css
+a {
+  b: progid:c(/**/ d);
+}
+
+<===>
+================================================================================
+<===> comment/progid/after_open_paren/silent/input.scss
+a {
+  b: progid:c(//
+    d);
+}
+
+<===> comment/progid/after_open_paren/silent/output.css
+a {
+  b: progid:c( d);
+}
+
+<===>
+================================================================================
+<===> comment/progid/before_close_paren/loud/input.scss
+a {b: progid:c(d /**/)}
+
+<===> comment/progid/before_close_paren/loud/output.css
+a {
+  b: progid:c(d /**/);
+}
+
+<===>
+================================================================================
+<===> comment/progid/before_close_paren/silent/input.scss
+a {
+  b: progid:c(d //
+    );
+}
+
+<===> comment/progid/before_close_paren/silent/output.css
+a {
+  b: progid:c(d  );
+}
diff --git a/spec/css/style_rule.hrx b/spec/css/style_rule.hrx
index fc8ed68ae..b7386e06c 100644
--- a/spec/css/style_rule.hrx
+++ b/spec/css/style_rule.hrx
@@ -1,15 +1,21 @@
 <===> comment/after_selector/loud/input.scss
-a /**/ {}
+a /**/ {b: c}
 
 <===> comment/after_selector/loud/output.css
+a {
+  b: c;
+}
 
 <===>
 ================================================================================
 <===> comment/after_selector/silent/input.scss
 a //
-  {}
+  {b: c}
 
 <===> comment/after_selector/silent/output.css
+a {
+  b: c;
+}
 
 <===>
 ================================================================================
diff --git a/spec/css/supports/comment.hrx b/spec/css/supports/comment.hrx
index 74a6bf5b6..d1d1077ff 100644
--- a/spec/css/supports/comment.hrx
+++ b/spec/css/supports/comment.hrx
@@ -1,27 +1,376 @@
 <===> before_query/loud/input.scss
-@supports /**/ (a: b) {}
+@supports /**/ (a: b) {c {d: e}}
 
 <===> before_query/loud/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
 
 <===>
 ================================================================================
 <===> before_query/silent/input.scss
 @supports //
-  (a: b) {}
+  (a: b) {c {d: e}}
 
 <===> before_query/silent/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/normal_prop/after_open_paren/loud/input.scss
+@supports (/**/ a: b) {c {d: e}}
+
+<===> declaration/normal_prop/after_open_paren/loud/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/normal_prop/after_open_paren/silent/input.scss
+@supports (//
+  a: b) {c {d: e}}
+
+<===> declaration/normal_prop/after_open_paren/silent/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/normal_prop/before_colon/loud/input.scss
+@supports (a /**/: b) {c {d: e}}
+
+<===> declaration/normal_prop/before_colon/loud/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/normal_prop/before_colon/silent/input.scss
+@supports (a //
+  : b) {c {d: e}}
+
+<===> declaration/normal_prop/before_colon/silent/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/normal_prop/after_colon/loud/input.scss
+@supports (a: /**/ b) {c {d: e}}
+
+<===> declaration/normal_prop/after_colon/loud/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/normal_prop/after_colon/silent/input.scss
+@supports (a: //
+  b) {c {d: e}}
+
+<===> declaration/normal_prop/after_colon/silent/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/normal_prop/before_close_paren/loud/input.scss
+@supports (a: b /**/) {c {d: e}}
+
+<===> declaration/normal_prop/before_close_paren/loud/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/normal_prop/before_close_paren/silent/input.scss
+@supports (a: b //
+  ) {c {d: e}}
+
+<===> declaration/normal_prop/before_close_paren/silent/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/custom_prop/after_open_paren/loud/input.scss
+@supports (/**/ --a: b) {c {d: e}}
+
+<===> declaration/custom_prop/after_open_paren/loud/output.css
+@supports (--a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/custom_prop/after_open_paren/silent/input.scss
+@supports (//
+  --a: b) {c {d: e}}
+
+<===> declaration/custom_prop/after_open_paren/silent/output.css
+@supports (--a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/custom_prop/before_colon/loud/input.scss
+@supports (--a /**/: b) {c {d: e}}
+
+<===> declaration/custom_prop/before_colon/loud/output.css
+@supports (--a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/custom_prop/before_colon/silent/input.scss
+@supports (--a //
+  : b) {c {d: e}}
+
+<===> declaration/custom_prop/before_colon/silent/output.css
+@supports (--a: b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/custom_prop/after_colon/loud/input.scss
+@supports (--a: /**/ b) {c {d: e}}
+
+<===> declaration/custom_prop/after_colon/loud/output.css
+@supports (--a: /**/ b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/custom_prop/after_colon/silent/input.scss
+@supports (--a: //
+  b) {c {d: e}}
+
+<===> declaration/custom_prop/after_colon/silent/output.css
+@supports (--a:  b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/custom_prop/before_close_paren/loud/input.scss
+@supports (--a: b /**/) {c {d: e}}
+
+<===> declaration/custom_prop/before_close_paren/loud/output.css
+@supports (--a: b /**/) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> declaration/custom_prop/before_close_paren/silent/input.scss
+@supports (--a: b //
+  ) {c {d: e}}
+
+<===> declaration/custom_prop/before_close_paren/silent/output.css
+@supports (--a: b  ) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> function/after_open_paren/loud/input.scss
+@supports a(/**/ b) {c {d: e}}
+
+<===> function/after_open_paren/loud/output.css
+@supports a(/**/ b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> function/after_open_paren/silent/input.scss
+@supports a(//
+  b) {c {d: e}}
+
+<===> function/after_open_paren/silent/output.css
+@supports a(
+  b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> function/before_close_paren/loud/input.scss
+@supports a(b /**/) {c {d: e}}
+
+<===> function/before_close_paren/loud/output.css
+@supports a(b /**/) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> function/before_close_paren/silent/input.scss
+@supports a(b //
+  ) {c {d: e}}
+
+<===> function/before_close_paren/silent/output.css
+@supports a(b 
+  ) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> anything/after_open_paren/loud/input.scss
+@supports (/**/ a b) {c {d: e}}
+
+<===> anything/after_open_paren/loud/output.css
+@supports (a b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> anything/after_open_paren/silent/input.scss
+@supports (//
+  a b) {c {d: e}}
+
+<===> anything/after_open_paren/silent/output.css
+@supports (a b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> anything/after_ident/loud/input.scss
+@supports (a /**/ b) {c {d: e}}
+
+<===> anything/after_ident/loud/output.css
+@supports (a /**/ b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> anything/after_ident/silent/input.scss
+@supports (a //
+  b) {c {d: e}}
+
+<===> anything/after_ident/silent/output.css
+@supports (a 
+  b) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> anything/before_close_paren/loud/input.scss
+@supports (a b /**/) {c {d: e}}
+
+<===> anything/before_close_paren/loud/output.css
+@supports (a b /**/) {
+  c {
+    d: e;
+  }
+}
+
+<===>
+================================================================================
+<===> anything/before_close_paren/silent/input.scss
+@supports (a b //
+  ) {c {d: e}}
+
+<===> anything/before_close_paren/silent/output.css
+@supports (a b 
+  ) {
+  c {
+    d: e;
+  }
+}
 
 <===>
 ================================================================================
 <===> after_query/loud/input.scss
-@supports (a: b) /**/ {}
+@supports (a: b) /**/ {c {d: e}}
 
 <===> after_query/loud/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
 
 <===>
 ================================================================================
 <===> after_query/silent/input.scss
 @supports (a: b) //
-  {}
+  {c {d: e}}
 
 <===> after_query/silent/output.css
+@supports (a: b) {
+  c {
+    d: e;
+  }
+}
diff --git a/spec/css/unknown_directive/comment.hrx b/spec/css/unknown_directive/comment.hrx
index c47a0ee37..2ac15252c 100644
--- a/spec/css/unknown_directive/comment.hrx
+++ b/spec/css/unknown_directive/comment.hrx
@@ -15,22 +15,14 @@
 
 <===>
 ================================================================================
-<===> no_children/after_value/loud/options.yml
-:todo:
-  - sass/dart-sass#2263
-
 <===> no_children/after_value/loud/input.scss
 @a b /**/
 
 <===> no_children/after_value/loud/output.css
-@a b;
+@a b /**/;
 
 <===>
 ================================================================================
-<===> no_children/after_value/silent/options.yml
-:todo:
-  - sass/dart-sass#2263
-
 <===> no_children/after_value/silent/input.scss
 @a b //
 
@@ -72,28 +64,20 @@
 
 <===>
 ================================================================================
-<===> children/after_value/loud/options.yml
-:todo:
-  - sass/dart-sass#2263
-
 <===> children/after_value/loud/input.scss
 @a b /**/ {}
 
 <===> children/after_value/loud/output.css
-@a b {};
+@a b /**/ {}
 
 <===>
 ================================================================================
-<===> children/after_value/silent/options.yml
-:todo:
-  - sass/dart-sass#2263
-
 <===> children/after_value/silent/input.scss
 @a b //
   {}
 
 <===> children/after_value/silent/output.css
-@a b {};
+@a b {}
 
 <===>
 ================================================================================
diff --git a/spec/css/unknown_directive/plain.hrx b/spec/css/unknown_directive/plain.hrx
index fd2cecd38..2e90f9a46 100644
--- a/spec/css/unknown_directive/plain.hrx
+++ b/spec/css/unknown_directive/plain.hrx
@@ -14,10 +14,7 @@
 
 <===> output.css
 @asdf .~@#$%^&*()_-+=[]|:<>,.?/;
-
 @asdf "f'o" 'b"r' url(baz) url("qux");
-
-@asdf foo //
+@asdf foo 
       bar;
-
 @asdf foo /* bar */ baz;
diff --git a/spec/directives/import/comment.hrx b/spec/directives/import/comment.hrx
index 12f05d1ba..f6d49bd9e 100644
--- a/spec/directives/import/comment.hrx
+++ b/spec/directives/import/comment.hrx
@@ -66,3 +66,101 @@
 <===> after_comma/silent/output.css
 @import "a.css";
 @import "b.css";
+
+<===>
+================================================================================
+<===> modifier/no_args/before/loud/input.scss
+@import "a.css" /**/ b
+
+<===> modifier/no_args/before/loud/output.css
+@import "a.css" b;
+
+<===>
+================================================================================
+<===> modifier/no_args/before/silent/input.scss
+@import "a.css" //
+  b
+
+<===> modifier/no_args/before/silent/output.css
+@import "a.css" b;
+
+<===>
+================================================================================
+<===> modifier/no_args/after/loud/input.scss
+@import "a.css" b /**/
+
+<===> modifier/no_args/after/loud/output.css
+@import "a.css" b;
+
+<===>
+================================================================================
+<===> modifier/no_args/after/silent/input.scss
+@import "a.css" b //
+
+<===> modifier/no_args/after/silent/output.css
+@import "a.css" b;
+
+<===>
+================================================================================
+<===> modifier/args/before/loud/input.scss
+@import "a.css" /**/ b(c)
+
+<===> modifier/args/before/loud/output.css
+@import "a.css" b(c);
+
+<===>
+================================================================================
+<===> modifier/args/before/silent/input.scss
+@import "a.css" //
+  b(c)
+
+<===> modifier/args/before/silent/output.css
+@import "a.css" b(c);
+
+<===>
+================================================================================
+<===> modifier/args/after_open_paren/loud/input.scss
+@import "a.css" b(/**/ c)
+
+<===> modifier/args/after_open_paren/loud/output.css
+@import "a.css" b(/**/ c);
+
+<===>
+================================================================================
+<===> modifier/args/after_open_paren/silent/input.scss
+@import "a.css" b(c)
+
+<===> modifier/args/after_open_paren/silent/output.css
+@import "a.css" b(c);
+
+<===>
+================================================================================
+<===> modifier/args/before_close_paren/loud/input.scss
+@import "a.css" b(c /**/)
+
+<===> modifier/args/before_close_paren/loud/output.css
+@import "a.css" b(c /**/);
+
+<===>
+================================================================================
+<===> modifier/args/before_close_paren/silent/input.scss
+@import "a.css" b(c)
+
+<===> modifier/args/before_close_paren/silent/output.css
+@import "a.css" b(c);
+
+<===>
+================================================================================
+<===> modifier/args/after/loud/input.scss
+@import "a.css" b(c) /**/
+
+<===> modifier/args/after/loud/output.css
+@import "a.css" b(c);
+
+<===>
+================================================================================
+<===> modifier/args/after/silent/input.scss
+@import "a.css" b(c) //
+
+<===> modifier/args/after/silent/output.css
+@import "a.css" b(c);
diff --git a/spec/libsass-closed-issues/issue_1263.hrx b/spec/libsass-closed-issues/issue_1263.hrx
index 7e94bf167..973b25c58 100644
--- a/spec/libsass-closed-issues/issue_1263.hrx
+++ b/spec/libsass-closed-issues/issue_1263.hrx
@@ -9,6 +9,6 @@ foo {
 foo {
   @apply;
   @apply (--bar);
-  @apply (  --bar  );
-  @apply (   --bar , --foo  );
+  @apply ( --bar );
+  @apply ( --bar , --foo );
 }