diff --git a/src/chisels.jl b/src/chisels.jl
index 0ca817c..ee2ac95 100644
--- a/src/chisels.jl
+++ b/src/chisels.jl
@@ -382,6 +382,17 @@ function second_leaf(node::Node)
     return nth_leaf(node, 2)
 end
 
+# TODO: This should probably be merged with kmatch or something...
+function peek_leafs(node::Node, leaf_kinds::Tuple)
+    for (i, leaf_kind) in pairs(leaf_kinds)
+        ith = nth_leaf(node, i)
+        if ith === nothing || kind(ith) !== leaf_kind
+            return false
+        end
+    end
+    return true
+end
+
 # Return number of non-whitespace kids, basically the length the equivalent
 # (expr::Expr).args
 function meta_nargs(node::Node)
diff --git a/src/runestone.jl b/src/runestone.jl
index 8dda47f..c48e0dc 100644
--- a/src/runestone.jl
+++ b/src/runestone.jl
@@ -2366,11 +2366,25 @@ function indent_listlike(
     # Next we expect the leading newline
     @assert multiline
     kid = kids[open_idx + 1]
+    idx_after_leading_nl = open_idx + 2
     if kind(kid) === K"NewlineWs" ||
-            kind(first_leaf(kid)) === K"NewlineWs"
+            kind(first_leaf(kid)) === K"NewlineWs" ||
+            peek_leafs(kid, KSet"Comment NewlineWs") || peek_leafs(kid, KSet"Whitespace Comment NewlineWs")
         # Newline or newlinde hidden in first item
         any_kid_changed && push!(kids′, kid)
         accept_node!(ctx, kid)
+    elseif kmatch(kids, KSet"Comment NewlineWs", open_idx + 1)
+        for i in (open_idx + 1):(open_idx + 2)
+            accept_node!(ctx, kids[i])
+            any_kid_changed && push!(kids′, kids[i])
+        end
+        idx_after_leading_nl = idx_after_leading_nl + 1
+    elseif kmatch(kids, KSet"Whitespace Comment NewlineWs", open_idx + 1)
+        for i in (open_idx + 1):(open_idx + 3)
+            accept_node!(ctx, kids[i])
+            any_kid_changed && push!(kids′, kids[i])
+        end
+        idx_after_leading_nl = idx_after_leading_nl + 2
     else
         # Need to insert a newline
         if kind(kid) === K"Whitespace"
@@ -2458,7 +2472,7 @@ function indent_listlike(
         end
     end
     # Bring all kids between the opening and closing token to the new list
-    for i in (open_idx + 2):(close_idx - 2)
+    for i in idx_after_leading_nl:(close_idx - 2)
         kid = kids[i]
         any_kid_changed && push!(kids′, kid)
         accept_node!(ctx, kid)
diff --git a/test/runtests.jl b/test/runtests.jl
index 041b689..76e56df 100644
--- a/test/runtests.jl
+++ b/test/runtests.jl
@@ -260,9 +260,13 @@ end
                 "$(o)\n    $(a),\n    $(b),\n$(c)"
             # trailing comments
             @test format_string("$(o)$(sp)# x\n$(sp)$(a)$(sp),$(sp)# a\n$(sp)$(b)$(sp)# b\n$(c)") ==
-                "$(o)\n    # x\n    $(a),$(csp)# a\n    $(b)$(tr)$(csp)# b\n$(c)"
+                "$(o)$(sp)# x\n    $(a),$(csp)# a\n    $(b)$(tr)$(csp)# b\n$(c)"
             @test format_string("$(o)$(sp)# x\n$(sp)$(a)$(sp),$(sp)# a\n$(sp)$(b),$(sp)# b\n$(c)") ==
-                "$(o)\n    # x\n    $(a),$(csp)# a\n    $(b),$(csp)# b\n$(c)"
+                "$(o)$(sp)# x\n    $(a),$(csp)# a\n    $(b),$(csp)# b\n$(c)"
+            @test format_string("$(o)$(sp)#= x =#$(sp)$(a)$(sp),$(sp)# a\n$(sp)$(b),$(sp)# b\n$(c)") ==
+                "$(o)\n    #= x =# $(a),$(csp)# a\n    $(b),$(csp)# b\n$(c)"
+            @test format_string("$(o)$(sp)#= x =#\n$(a)$(sp),$(sp)# a\n$(sp)$(b),$(sp)# b\n$(c)") ==
+                "$(o)$(sp)#= x =#\n    $(a),$(csp)# a\n    $(b),$(csp)# b\n$(c)"
             # comments on separate lines between items
             @test format_string("$(o)\n# a\n$(a)$(sp),\n# b\n$(b)\n$(c)") ==
                 "$(o)\n    # a\n    $(a),\n    # b\n    $(b)$(tr)\n$(c)"