diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/actual.css b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/actual.css
new file mode 100644
index 0000000000..18ba4145c5
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/actual.css
@@ -0,0 +1 @@
+:host-context(.foo) {}
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/config.json b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/config.json
new file mode 100644
index 0000000000..b93f34675c
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/config.json
@@ -0,0 +1,4 @@
+{
+  "disableSyntheticShadowSupport": true,
+  "scoped": true
+}
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/error.json b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/error.json
new file mode 100644
index 0000000000..61ba9a9f3f
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector-scoped/error.json
@@ -0,0 +1,6 @@
+{
+    "name": "CssSyntaxError",
+    "reason": "Invalid usage of unsupported selector \":host-context\". This selector is only supported in non-scoped CSS where the `disableSyntheticShadowSupport` flag is set to true.",
+    "column": 1,
+    "line": 1
+}
\ No newline at end of file
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/actual.css b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/actual.css
new file mode 100644
index 0000000000..18ba4145c5
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/actual.css
@@ -0,0 +1 @@
+:host-context(.foo) {}
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/config.json b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/config.json
new file mode 100644
index 0000000000..0a910de825
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/config.json
@@ -0,0 +1,3 @@
+{
+  "disableSyntheticShadowSupport": true
+}
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/expected.js b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/expected.js
new file mode 100644
index 0000000000..252029db11
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-host-context-selector/expected.js
@@ -0,0 +1,12 @@
+function stylesheet() {
+  var token;
+  var useActualHostSelector = true;
+  var useNativeDirPseudoclass = true;
+  var shadowSelector = token ? ("[" + token + "]") : "";
+  var hostSelector = token ? ("[" + token + "-host]") : "";
+  var suffixToken = token ? ("-" + token) : "";
+  return ":host-context(.foo)" + shadowSelector + " {}";
+  /*LWC compiler vX.X.X*/
+}
+stylesheet.$nativeOnly$ = true;
+export default [stylesheet];
\ No newline at end of file
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/actual.css b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/actual.css
new file mode 100644
index 0000000000..052bf632f1
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/actual.css
@@ -0,0 +1 @@
+:root {}
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/config.json b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/config.json
new file mode 100644
index 0000000000..b93f34675c
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/config.json
@@ -0,0 +1,4 @@
+{
+  "disableSyntheticShadowSupport": true,
+  "scoped": true
+}
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/error.json b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/error.json
new file mode 100644
index 0000000000..297146009e
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector-scoped/error.json
@@ -0,0 +1,6 @@
+{
+    "name": "CssSyntaxError",
+    "reason": "Invalid usage of unsupported selector \":root\". This selector is only supported in non-scoped CSS where the `disableSyntheticShadowSupport` flag is set to true.",
+    "column": 1,
+    "line": 1
+}
\ No newline at end of file
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/actual.css b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/actual.css
new file mode 100644
index 0000000000..052bf632f1
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/actual.css
@@ -0,0 +1 @@
+:root {}
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/config.json b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/config.json
new file mode 100644
index 0000000000..0a910de825
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/config.json
@@ -0,0 +1,3 @@
+{
+  "disableSyntheticShadowSupport": true
+}
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/expected.js b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/expected.js
new file mode 100644
index 0000000000..42d7d5cbc3
--- /dev/null
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/disable-synthetic-shadow-support-root-selector/expected.js
@@ -0,0 +1,12 @@
+function stylesheet() {
+  var token;
+  var useActualHostSelector = true;
+  var useNativeDirPseudoclass = true;
+  var shadowSelector = token ? ("[" + token + "]") : "";
+  var hostSelector = token ? ("[" + token + "-host]") : "";
+  var suffixToken = token ? ("-" + token) : "";
+  return ":root" + shadowSelector + " {}";
+  /*LWC compiler vX.X.X*/
+}
+stylesheet.$nativeOnly$ = true;
+export default [stylesheet];
\ No newline at end of file
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/unsupported-host-context-selector/error.json b/packages/@lwc/style-compiler/src/__tests__/fixtures/unsupported-host-context-selector/error.json
index f5131d5bdf..61ba9a9f3f 100644
--- a/packages/@lwc/style-compiler/src/__tests__/fixtures/unsupported-host-context-selector/error.json
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/unsupported-host-context-selector/error.json
@@ -1,6 +1,6 @@
 {
     "name": "CssSyntaxError",
-    "reason": "Invalid usage of unsupported selector \":host-context\".",
+    "reason": "Invalid usage of unsupported selector \":host-context\". This selector is only supported in non-scoped CSS where the `disableSyntheticShadowSupport` flag is set to true.",
     "column": 1,
     "line": 1
 }
\ No newline at end of file
diff --git a/packages/@lwc/style-compiler/src/__tests__/fixtures/unsupported-root-selector/error.json b/packages/@lwc/style-compiler/src/__tests__/fixtures/unsupported-root-selector/error.json
index ba796fd202..297146009e 100644
--- a/packages/@lwc/style-compiler/src/__tests__/fixtures/unsupported-root-selector/error.json
+++ b/packages/@lwc/style-compiler/src/__tests__/fixtures/unsupported-root-selector/error.json
@@ -1,6 +1,6 @@
 {
     "name": "CssSyntaxError",
-    "reason": "Invalid usage of unsupported selector \":root\".",
+    "reason": "Invalid usage of unsupported selector \":root\". This selector is only supported in non-scoped CSS where the `disableSyntheticShadowSupport` flag is set to true.",
     "column": 1,
     "line": 1
 }
\ No newline at end of file
diff --git a/packages/@lwc/style-compiler/src/postcss-lwc-plugin.ts b/packages/@lwc/style-compiler/src/postcss-lwc-plugin.ts
index 92171b694a..812110ff7d 100644
--- a/packages/@lwc/style-compiler/src/postcss-lwc-plugin.ts
+++ b/packages/@lwc/style-compiler/src/postcss-lwc-plugin.ts
@@ -32,15 +32,20 @@ function selectorProcessorFactory(transformConfig: SelectorScopingConfig) {
 export default function postCssLwcPlugin(options: {
     scoped: boolean;
     apiVersion: APIVersion;
+    disableSyntheticShadowSupport: boolean;
 }): TransformCallback {
     // We need 2 types of selectors processors, since transforming the :host selector make the selector
     // unusable when used in the context of the native shadow and vice-versa.
     // This distinction also applies to light DOM in scoped (synthetic-like) vs unscoped (native-like) mode.
     const nativeShadowSelectorProcessor = selectorProcessorFactory({
         transformHost: false,
+        disableSyntheticShadowSupport: options.disableSyntheticShadowSupport,
+        scoped: options.scoped,
     });
     const syntheticShadowSelectorProcessor = selectorProcessorFactory({
         transformHost: true,
+        disableSyntheticShadowSupport: options.disableSyntheticShadowSupport,
+        scoped: options.scoped,
     });
 
     return (root, result) => {
diff --git a/packages/@lwc/style-compiler/src/selector-scoping/transform.ts b/packages/@lwc/style-compiler/src/selector-scoping/transform.ts
index 25b3a44c5e..3558bece3a 100644
--- a/packages/@lwc/style-compiler/src/selector-scoping/transform.ts
+++ b/packages/@lwc/style-compiler/src/selector-scoping/transform.ts
@@ -27,6 +27,10 @@ type ChildNode = Exclude<Node, Selector>;
 export interface SelectorScopingConfig {
     /** When set to true, the :host selector gets replace with the the scoping token. */
     transformHost: boolean;
+    /** When set to true, the synthetic shadow support is disabled. */
+    disableSyntheticShadowSupport: boolean;
+    /** When set to true, the selector is scoped. */
+    scoped: boolean;
 }
 
 function isHostPseudoClass(node: Node): node is Pseudo {
@@ -145,7 +149,10 @@ function transformHost(selector: Selector) {
 }
 
 export default function transformSelector(root: Root, transformConfig: SelectorScopingConfig) {
-    validateSelectors(root);
+    validateSelectors(
+        root,
+        transformConfig.disableSyntheticShadowSupport && !transformConfig.scoped
+    );
 
     root.each(scopeSelector);
 
diff --git a/packages/@lwc/style-compiler/src/selector-scoping/validate.ts b/packages/@lwc/style-compiler/src/selector-scoping/validate.ts
index 036f2bc1a0..d0f2a9b14f 100644
--- a/packages/@lwc/style-compiler/src/selector-scoping/validate.ts
+++ b/packages/@lwc/style-compiler/src/selector-scoping/validate.ts
@@ -10,7 +10,7 @@ const DEPRECATED_SELECTORS = new Set(['/deep/', '::shadow', '>>>']);
 const UNSUPPORTED_SELECTORS = new Set([':root', ':host-context']);
 const TEMPLATE_DIRECTIVES = [/^key$/, /^lwc:*/, /^if:*/, /^for:*/, /^iterator:*/];
 
-function validateSelectors(root: Root) {
+function validateSelectors(root: Root, native: boolean) {
     root.walk((node) => {
         const { value, sourceIndex } = node;
 
@@ -24,11 +24,14 @@ function validateSelectors(root: Root) {
             }
 
             // Ensure the selector doesn't use an unsupported selector.
-            if (UNSUPPORTED_SELECTORS.has(value)) {
-                throw root.error(`Invalid usage of unsupported selector "${value}".`, {
-                    index: sourceIndex,
-                    word: value,
-                });
+            if (!native && UNSUPPORTED_SELECTORS.has(value)) {
+                throw root.error(
+                    `Invalid usage of unsupported selector "${value}". This selector is only supported in non-scoped CSS where the \`disableSyntheticShadowSupport\` flag is set to true.`,
+                    {
+                        index: sourceIndex,
+                        word: value,
+                    }
+                );
             }
         }
     });
@@ -55,7 +58,7 @@ function validateAttribute(root: Root) {
     });
 }
 
-export default function validate(root: Root) {
-    validateSelectors(root);
+export default function validate(root: Root, native: boolean) {
+    validateSelectors(root, native);
     validateAttribute(root);
 }
diff --git a/packages/@lwc/style-compiler/src/transform.ts b/packages/@lwc/style-compiler/src/transform.ts
index e82020feb1..52f50fe6a2 100644
--- a/packages/@lwc/style-compiler/src/transform.ts
+++ b/packages/@lwc/style-compiler/src/transform.ts
@@ -53,8 +53,9 @@ export function transform(src: string, id: string, config: Config = {}): { code:
 
     const scoped = !!config.scoped;
     const apiVersion = getAPIVersionFromNumber(config.apiVersion);
+    const disableSyntheticShadowSupport = !!config.disableSyntheticShadowSupport;
 
-    const plugins = [postcssLwc({ scoped, apiVersion })];
+    const plugins = [postcssLwc({ scoped, apiVersion, disableSyntheticShadowSupport })];
 
     const result = postcss(plugins).process(src, { from: id }).sync();