diff --git a/NEWS.md b/NEWS.md
index 23cb10eb..e24e5b2e 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -1,5 +1,10 @@
 # htmltools (development version)
 
+## Bug fixes
+
+* `bindFillRole()` now attaches its `HTMLDependency()` to fill items, thus reducing the possibility of filling layout breaking due to missing CSS. (#421) 
+
+
 # htmltools 0.5.7
 
 ## New Features
diff --git a/R/fill.R b/R/fill.R
index 2309de64..710b51fa 100644
--- a/R/fill.R
+++ b/R/fill.R
@@ -91,7 +91,7 @@ bindFillRole <- function(x, ..., item = FALSE, container = FALSE, overwrite = FA
     class = if (container) "html-fill-container"
   )
 
-  if (container) {
+  if (container || item) {
     x <- attachDependencies(x, fillDependencies(), append = TRUE)
   }
 
diff --git a/tests/testthat/test-fill.R b/tests/testthat/test-fill.R
index fef0cdff..a33e1038 100644
--- a/tests/testthat/test-fill.R
+++ b/tests/testthat/test-fill.R
@@ -8,11 +8,13 @@ test_that("asFillContainer() and asFillItem()", {
   expect_true(
     doRenderTags(x) == "<div class=\"html-fill-container\"></div>"
   )
+  expect_equal(htmlDependencies(x), list(fillDependencies()))
 
   x <- bindFillRole(div(), item = TRUE)
   expect_true(
     doRenderTags(x) == "<div class=\"html-fill-item\"></div>"
   )
+  expect_equal(htmlDependencies(x), list(fillDependencies()))
 
   x <- bindFillRole(x, container = TRUE, overwrite = TRUE)
   expect_true(