diff --git a/source/h1_stream.c b/source/h1_stream.c
index a43bd37fb..1687ddb5f 100644
--- a/source/h1_stream.c
+++ b/source/h1_stream.c
@@ -431,6 +431,34 @@ struct aws_h1_stream *aws_h1_stream_new_request(
         stream->thread_data.is_final_stream = true;
     }
 
+    struct aws_http_headers *headers = aws_http_message_get_headers(options->request);
+
+    /* Log the headers that we are sending out. */
+    for (size_t i = 0; i < aws_http_headers_count(headers); i++) {
+        struct aws_http_header header;
+        aws_http_headers_get_index(headers, i, &header);
+        enum aws_http_header_name name_enum = aws_http_str_to_header_name(header.name);
+        switch (name_enum) {
+            case AWS_HTTP_HEADER_AUTHORIZATION:
+                /* Sensitive header, do not log the value of the header */
+                AWS_LOGF_TRACE(
+                    AWS_LS_HTTP_STREAM,
+                    "id=%p: Sending header: " PRInSTR ": ***",
+                    (void *)&stream->base,
+                    AWS_BYTE_CURSOR_PRI(header.name));
+                break;
+            default:
+                /* Log the headers we are sending out */
+                AWS_LOGF_TRACE(
+                    AWS_LS_HTTP_STREAM,
+                    "id=%p: Sending header: " PRInSTR ": " PRInSTR "",
+                    (void *)&stream->base,
+                    AWS_BYTE_CURSOR_PRI(header.name),
+                    AWS_BYTE_CURSOR_PRI(header.value));
+                break;
+        }
+    }
+
     stream->synced_data.using_chunked_encoding = stream->thread_data.encoder_message.has_chunked_encoding_header;
 
     return stream;
diff --git a/source/h2_stream.c b/source/h2_stream.c
index 4a5f93649..74655853f 100644
--- a/source/h2_stream.c
+++ b/source/h2_stream.c
@@ -750,6 +750,45 @@ int aws_h2_stream_on_activated(struct aws_h2_stream *stream, enum aws_h2_stream_
             connection->thread_data.settings_self[AWS_HTTP2_SETTINGS_INITIAL_WINDOW_SIZE] / 2;
     }
 
+    /* Log the headers that we are sending out. */
+    for (size_t i = 0; i < aws_http_headers_count(h2_headers); i++) {
+        struct aws_http_header header;
+        aws_http_headers_get_index(h2_headers, i, &header);
+        enum aws_http_header_name name_enum = aws_http_str_to_header_name(header.name);
+        switch (name_enum) {
+            case AWS_HTTP_HEADER_CONNECTION:
+            case AWS_HTTP_HEADER_TRANSFER_ENCODING:
+            case AWS_HTTP_HEADER_UPGRADE:
+            case AWS_HTTP_HEADER_KEEP_ALIVE:
+            case AWS_HTTP_HEADER_PROXY_CONNECTION:
+                /**
+                 * An endpoint MUST NOT generate an HTTP/2 message containing connection-specific header fields.
+                 * (RFC=9113 8.2.2)
+                 */
+                AWS_H2_STREAM_LOGF(
+                    TRACE,
+                    stream,
+                    "Found connection-specific header that is allowed in HTTP/2. : " PRInSTR ": " PRInSTR "",
+                    AWS_BYTE_CURSOR_PRI(header.name),
+                    AWS_BYTE_CURSOR_PRI(header.value));
+                aws_raise_error(AWS_ERROR_HTTP_INVALID_HEADER_FIELD);
+                goto error;
+            case AWS_HTTP_HEADER_AUTHORIZATION:
+                /* Sensitive header, do not log the value of the header */
+                AWS_H2_STREAM_LOGF(TRACE, stream, "Sending header: " PRInSTR ": ***", AWS_BYTE_CURSOR_PRI(header.name));
+                break;
+            default:
+                /* Log the headers we are sending out */
+                AWS_H2_STREAM_LOGF(
+                    TRACE,
+                    stream,
+                    "Sending header: " PRInSTR ": " PRInSTR "",
+                    AWS_BYTE_CURSOR_PRI(header.name),
+                    AWS_BYTE_CURSOR_PRI(header.value));
+                break;
+        }
+    }
+
     if (with_data) {
         /* If stream has DATA to send, put it in the outgoing_streams_list, and we'll send data later */
         stream->thread_data.state = AWS_H2_STREAM_STATE_OPEN;
diff --git a/source/request_response.c b/source/request_response.c
index dbd5214e7..6f290b0e1 100644
--- a/source/request_response.c
+++ b/source/request_response.c
@@ -1036,15 +1036,17 @@ struct aws_http_message *aws_http2_message_new_from_http1(
         struct aws_byte_cursor lower_name_cursor = aws_byte_cursor_from_buf(&lower_name_buf);
         enum aws_http_header_name name_enum = aws_http_lowercase_str_to_header_name(lower_name_cursor);
         switch (name_enum) {
+            /**
+             * An intermediary transforming an HTTP/1.x message to HTTP/2 MUST remove connection-specific header
+             * fields as discussed in Section 7.6.1 of [HTTP]. (RFC=9113 8.2.2)
+             */
+            case AWS_HTTP_HEADER_CONNECTION:
             case AWS_HTTP_HEADER_TRANSFER_ENCODING:
             case AWS_HTTP_HEADER_UPGRADE:
             case AWS_HTTP_HEADER_KEEP_ALIVE:
             case AWS_HTTP_HEADER_PROXY_CONNECTION:
+            /* Host has been converted to :authority pseudo header, skip it as well. */
             case AWS_HTTP_HEADER_HOST:
-                /**
-                 * An intermediary transforming an HTTP/1.x message to HTTP/2 MUST remove connection-specific header
-                 * fields as discussed in Section 7.6.1 of [HTTP]. (RFC=9113 8.2.2)
-                 */
                 AWS_LOGF_TRACE(
                     AWS_LS_HTTP_GENERAL,
                     "Skip connection-specific headers - \"%.*s\" ",