diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/error.txt b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/error.txt
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/expected.html b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/expected.html
new file mode 100644
index 0000000000..f31c0fe31f
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/expected.html
@@ -0,0 +1,19 @@
+<x-stylish class="lwc-72njdrv8nr1-host">
+  <template shadowrootmode="open">
+    <style class="lwc-72njdrv8nr1" type="text/css">
+      h1 {border: 1px solid goldenrod;}
+    </style>
+    <style class="lwc-72njdrv8nr1" type="text/css">
+      h1.lwc-72njdrv8nr1 {outline: 2px solid chartreuse;}
+    </style>
+    <style class="lwc-72njdrv8nr1" type="text/css">
+      h1 {background: royalblue;}
+    </style>
+    <style class="lwc-72njdrv8nr1" type="text/css">
+      h1.lwc-72njdrv8nr1 {color: cornsilk;}
+    </style>
+    <h1 class="lwc-72njdrv8nr1">
+      hello
+    </h1>
+  </template>
+</x-stylish>
\ No newline at end of file
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/index.js b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/index.js
new file mode 100644
index 0000000000..e731a3c77c
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/index.js
@@ -0,0 +1,3 @@
+export const tagName = 'x-stylish';
+export { default } from 'x/stylish';
+export * from 'x/stylish';
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.css b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.css
new file mode 100644
index 0000000000..efb740258d
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.css
@@ -0,0 +1,3 @@
+h1 {
+    border: 1px solid goldenrod;
+}
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.html b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.html
new file mode 100644
index 0000000000..e40c3bd251
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.html
@@ -0,0 +1,3 @@
+<template>
+    <h1>hello</h1>
+</template>
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.scoped.css b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.scoped.css
new file mode 100644
index 0000000000..f69629f169
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/dazzling.scoped.css
@@ -0,0 +1,3 @@
+h1 {
+    outline: 2px solid chartreuse;
+}
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/glamorous.css b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/glamorous.css
new file mode 100644
index 0000000000..1a8301a1e7
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/glamorous.css
@@ -0,0 +1,3 @@
+h1 {
+    background: royalblue;
+}
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/snazzy.scoped.css b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/snazzy.scoped.css
new file mode 100644
index 0000000000..a6650aec13
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/snazzy.scoped.css
@@ -0,0 +1,3 @@
+h1 {
+    color: cornsilk;
+}
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/stylish.js b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/stylish.js
new file mode 100644
index 0000000000..2a728b5297
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets-dynamic-render/modules/x/stylish/stylish.js
@@ -0,0 +1,12 @@
+import { LightningElement } from 'lwc';
+import glamorous from './glamorous.css'
+import snazzy from './snazzy.scoped.css'
+import dazzling from './dazzling.html'
+
+export default class extends LightningElement {
+  static stylesheets = [glamorous, snazzy]
+
+  render() {
+    return dazzling;
+  }
+}
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/error.txt b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/error.txt
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/expected.html b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/expected.html
new file mode 100644
index 0000000000..170351b968
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/expected.html
@@ -0,0 +1,13 @@
+<x-stylish class="lwc-1l667kdb4s5-host">
+  <template shadowrootmode="open">
+    <style class="lwc-1l667kdb4s5" type="text/css">
+      h1 {background: royalblue;}
+    </style>
+    <style class="lwc-1l667kdb4s5" type="text/css">
+      h1.lwc-1l667kdb4s5 {color: cornsilk;}
+    </style>
+    <h1 class="lwc-1l667kdb4s5">
+      hello
+    </h1>
+  </template>
+</x-stylish>
\ No newline at end of file
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/index.js b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/index.js
new file mode 100644
index 0000000000..e731a3c77c
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/index.js
@@ -0,0 +1,3 @@
+export const tagName = 'x-stylish';
+export { default } from 'x/stylish';
+export * from 'x/stylish';
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/glamorous.css b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/glamorous.css
new file mode 100644
index 0000000000..1a8301a1e7
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/glamorous.css
@@ -0,0 +1,3 @@
+h1 {
+    background: royalblue;
+}
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/snazzy.scoped.css b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/snazzy.scoped.css
new file mode 100644
index 0000000000..a6650aec13
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/snazzy.scoped.css
@@ -0,0 +1,3 @@
+h1 {
+    color: cornsilk;
+}
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/stylish.html b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/stylish.html
new file mode 100644
index 0000000000..e40c3bd251
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/stylish.html
@@ -0,0 +1,3 @@
+<template>
+    <h1>hello</h1>
+</template>
diff --git a/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/stylish.js b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/stylish.js
new file mode 100644
index 0000000000..257997fe1a
--- /dev/null
+++ b/packages/@lwc/engine-server/src/__tests__/fixtures/static-stylesheets/modules/x/stylish/stylish.js
@@ -0,0 +1,7 @@
+import { LightningElement } from 'lwc';
+import glamorous from './glamorous.css'
+import snazzy from './snazzy.scoped.css'
+
+export default class extends LightningElement {
+  static stylesheets = [glamorous, snazzy]
+}