diff --git a/source/extensions/filters/http/common/compressor/compressor.cc b/source/extensions/filters/http/common/compressor/compressor.cc
index f417b890b5e27..5242ee31f4197 100644
--- a/source/extensions/filters/http/common/compressor/compressor.cc
+++ b/source/extensions/filters/http/common/compressor/compressor.cc
@@ -68,13 +68,8 @@ Http::FilterHeadersStatus CompressorFilter::decodeHeaders(Http::RequestHeaderMap
     accept_encoding_ = std::make_unique<std::string>(accept_encoding->value().getStringView());
   }
 
-  if (config_->enabled()) {
-    skip_compression_ = false;
-    if (config_->removeAcceptEncodingHeader()) {
-      headers.removeAcceptEncoding();
-    }
-  } else {
-    config_->stats().not_compressed_.inc();
+  if (config_->enabled() && config_->removeAcceptEncodingHeader()) {
+    headers.removeAcceptEncoding();
   }
 
   return Http::FilterHeadersStatus::Continue;
@@ -105,10 +100,11 @@ void CompressorFilter::setDecoderFilterCallbacks(Http::StreamDecoderFilterCallba
 
 Http::FilterHeadersStatus CompressorFilter::encodeHeaders(Http::ResponseHeaderMap& headers,
                                                           bool end_stream) {
-  if (!end_stream && !skip_compression_ && isMinimumContentLength(headers) &&
+  if (!end_stream && config_->enabled() && isMinimumContentLength(headers) &&
       isAcceptEncodingAllowed(headers) && isContentTypeAllowed(headers) &&
       !hasCacheControlNoTransform(headers) && isEtagAllowed(headers) &&
       isTransferEncodingAllowed(headers) && !headers.ContentEncoding()) {
+    skip_compression_ = false;
     sanitizeEtagHeader(headers);
     insertVaryHeader(headers);
     headers.removeContentLength();
@@ -116,8 +112,7 @@ Http::FilterHeadersStatus CompressorFilter::encodeHeaders(Http::ResponseHeaderMa
     config_->stats().compressed_.inc();
     // Finally instantiate the compressor.
     compressor_ = config_->makeCompressor();
-  } else if (!skip_compression_) {
-    skip_compression_ = true;
+  } else {
     config_->stats().not_compressed_.inc();
   }
   return Http::FilterHeadersStatus::Continue;
diff --git a/test/extensions/filters/http/common/compressor/compressor_filter_test.cc b/test/extensions/filters/http/common/compressor/compressor_filter_test.cc
index 6f4379299330a..e6610b8149789 100644
--- a/test/extensions/filters/http/common/compressor/compressor_filter_test.cc
+++ b/test/extensions/filters/http/common/compressor/compressor_filter_test.cc
@@ -174,7 +174,9 @@ TEST_F(CompressorFilterTest, DecodeHeadersWithRuntimeDisabled) {
   }
 }
 )EOF");
-  EXPECT_CALL(runtime_.snapshot_, getBoolean("foo_key", true)).WillOnce(Return(false));
+  EXPECT_CALL(runtime_.snapshot_, getBoolean("foo_key", true))
+      .Times(2)
+      .WillRepeatedly(Return(false));
   doRequest({{":method", "get"}, {"accept-encoding", "deflate, test"}}, false);
   doResponseNoCompression({{":method", "get"}, {"content-length", "256"}});
 }
diff --git a/test/extensions/filters/http/gzip/gzip_filter_test.cc b/test/extensions/filters/http/gzip/gzip_filter_test.cc
index 28035fd6510e0..6d451e436b9bb 100644
--- a/test/extensions/filters/http/gzip/gzip_filter_test.cc
+++ b/test/extensions/filters/http/gzip/gzip_filter_test.cc
@@ -176,7 +176,9 @@ TEST_F(GzipFilterTest, RuntimeDisabled) {
   }
 }
 )EOF");
-  EXPECT_CALL(runtime_.snapshot_, getBoolean("foo_key", true)).WillOnce(Return(false));
+  EXPECT_CALL(runtime_.snapshot_, getBoolean("foo_key", true))
+      .Times(2)
+      .WillRepeatedly(Return(false));
   doRequest({{":method", "get"}, {"accept-encoding", "deflate, gzip"}}, false);
   doResponseNoCompression({{":method", "get"}, {"content-length", "256"}});
 }