diff --git a/git-curl-compat.h b/git-curl-compat.h
index fd96b3cdff..e1d0bdd273 100644
--- a/git-curl-compat.h
+++ b/git-curl-compat.h
@@ -126,6 +126,15 @@
 #define GIT_CURL_HAVE_CURLSSLSET_NO_BACKENDS
 #endif
 
+/**
+ * Versions before curl 7.66.0 (September 2019) required manually setting the
+ * transfer-encoding for a streaming POST; after that this is handled
+ * automatically.
+ */
+#if LIBCURL_VERSION_NUM < 0x074200
+#define GIT_CURL_NEED_TRANSFER_ENCODING_HEADER
+#endif
+
 /**
  * CURLOPT_PROTOCOLS_STR and CURLOPT_REDIR_PROTOCOLS_STR were added in 7.85.0,
  * released in August 2022.
diff --git a/remote-curl.c b/remote-curl.c
index 1161dc7fed..603c11ba66 100644
--- a/remote-curl.c
+++ b/remote-curl.c
@@ -1,4 +1,5 @@
 #include "git-compat-util.h"
+#include "git-curl-compat.h"
 #include "config.h"
 #include "environment.h"
 #include "gettext.h"
@@ -960,7 +961,9 @@ static int post_rpc(struct rpc_state *rpc, int stateless_connect, int flush_rece
 		/* The request body is large and the size cannot be predicted.
 		 * We must use chunked encoding to send it.
 		 */
+#ifdef GIT_CURL_NEED_TRANSFER_ENCODING_HEADER
 		headers = curl_slist_append(headers, "Transfer-Encoding: chunked");
+#endif
 		rpc->initial_buffer = 1;
 		curl_easy_setopt(slot->curl, CURLOPT_READFUNCTION, rpc_out);
 		curl_easy_setopt(slot->curl, CURLOPT_INFILE, rpc);