diff --git a/spec/test-outputs/www-eks-integration.out.vcl b/spec/test-outputs/www-eks-integration.out.vcl
index d1cf1e8e..5aeca122 100644
--- a/spec/test-outputs/www-eks-integration.out.vcl
+++ b/spec/test-outputs/www-eks-integration.out.vcl
@@ -58,6 +58,13 @@ sub vcl_recv {
 
   
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";
diff --git a/spec/test-outputs/www-eks-production.out.vcl b/spec/test-outputs/www-eks-production.out.vcl
index a0a1e1d6..14fb1523 100644
--- a/spec/test-outputs/www-eks-production.out.vcl
+++ b/spec/test-outputs/www-eks-production.out.vcl
@@ -151,6 +151,13 @@ sub vcl_recv {
 
   
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";
diff --git a/spec/test-outputs/www-eks-staging.out.vcl b/spec/test-outputs/www-eks-staging.out.vcl
index 63333b9a..c313e5f5 100644
--- a/spec/test-outputs/www-eks-staging.out.vcl
+++ b/spec/test-outputs/www-eks-staging.out.vcl
@@ -159,6 +159,13 @@ sub vcl_recv {
 
   
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";
diff --git a/spec/test-outputs/www-eks-test.out.vcl b/spec/test-outputs/www-eks-test.out.vcl
index c6d9bd0c..26b5311b 100644
--- a/spec/test-outputs/www-eks-test.out.vcl
+++ b/spec/test-outputs/www-eks-test.out.vcl
@@ -55,6 +55,13 @@ sub vcl_recv {
 
   
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";
diff --git a/spec/test-outputs/www-integration.out.vcl b/spec/test-outputs/www-integration.out.vcl
index d1cf1e8e..5aeca122 100644
--- a/spec/test-outputs/www-integration.out.vcl
+++ b/spec/test-outputs/www-integration.out.vcl
@@ -58,6 +58,13 @@ sub vcl_recv {
 
   
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";
diff --git a/spec/test-outputs/www-production.out.vcl b/spec/test-outputs/www-production.out.vcl
index a0a1e1d6..14fb1523 100644
--- a/spec/test-outputs/www-production.out.vcl
+++ b/spec/test-outputs/www-production.out.vcl
@@ -151,6 +151,13 @@ sub vcl_recv {
 
   
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";
diff --git a/spec/test-outputs/www-staging.out.vcl b/spec/test-outputs/www-staging.out.vcl
index 63333b9a..c313e5f5 100644
--- a/spec/test-outputs/www-staging.out.vcl
+++ b/spec/test-outputs/www-staging.out.vcl
@@ -159,6 +159,13 @@ sub vcl_recv {
 
   
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";
diff --git a/spec/test-outputs/www-test.out.vcl b/spec/test-outputs/www-test.out.vcl
index c6d9bd0c..26b5311b 100644
--- a/spec/test-outputs/www-test.out.vcl
+++ b/spec/test-outputs/www-test.out.vcl
@@ -55,6 +55,13 @@ sub vcl_recv {
 
   
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";
diff --git a/vcl_templates/www.vcl.erb b/vcl_templates/www.vcl.erb
index 6bcbe2fc..cb6ef709 100644
--- a/vcl_templates/www.vcl.erb
+++ b/vcl_templates/www.vcl.erb
@@ -202,6 +202,13 @@ sub vcl_recv {
   }
   <% end %>
 
+  # Strip Accept-Encoding header if the content is already compressed
+  if (req.http.Accept-Encoding) {
+    if (req.url ~ "\.(jpeg|jpg|png|gif|gz|tgz|bz2|tbz|zip|flv|pdf|mp3|ogg)$") {
+      remove req.http.Accept-Encoding;
+    }
+  }
+
   # Force SSL.
   if (!req.http.Fastly-SSL) {
      error 801 "Force SSL";