diff --git a/src/mongocrypt-ctx-rewrap-many-datakey.c b/src/mongocrypt-ctx-rewrap-many-datakey.c
index 32fc6f793..e24865c22 100644
--- a/src/mongocrypt-ctx-rewrap-many-datakey.c
+++ b/src/mongocrypt-ctx-rewrap-many-datakey.c
@@ -136,6 +136,18 @@ static mongocrypt_kms_ctx_t *_next_kms_ctx_encrypt(mongocrypt_ctx_t *ctx) {
     mongocrypt_ctx_t *dkctx = NULL;
 
     BSON_ASSERT_PARAM(ctx);
+    /* Check if any need retry */
+    {
+        _mongocrypt_ctx_rmd_datakey_t *it = rmdctx->datakeys;
+        while (it != NULL) {
+            _mongocrypt_ctx_datakey_t *dkctx = (_mongocrypt_ctx_datakey_t *)it->dkctx;
+            if (dkctx->kms.should_retry) {
+                dkctx->kms.should_retry = false; // Reset retry state.
+                return &dkctx->kms;
+            }
+            it = it->next;
+        }
+    }
 
     /* No more datakey contexts requiring KMS. */
     if (!rmdctx->datakeys_iter) {
diff --git a/test/test-mongocrypt-ctx-rewrap-many-datakey.c b/test/test-mongocrypt-ctx-rewrap-many-datakey.c
index 69381db0b..e725f152f 100644
--- a/test/test-mongocrypt-ctx-rewrap-many-datakey.c
+++ b/test/test-mongocrypt-ctx-rewrap-many-datakey.c
@@ -570,6 +570,33 @@ static void _test_rewrap_many_datakey_need_kms_retry(_mongocrypt_tester_t *teste
     ASSERT(mongocrypt_kms_ctx_bytes_needed(kms) == 0);
     ASSERT_OK(mongocrypt_ctx_kms_done(ctx), ctx);
     ASSERT_STATE_EQUAL(mongocrypt_ctx_state(ctx), MONGOCRYPT_CTX_NEED_KMS); // To encrypt.
+    mongocrypt_ctx_destroy(ctx);
+
+    /* Clear key cache. */
+    mongocrypt_destroy(crypt);
+    crypt = _mongocrypt_tester_mongocrypt(TESTER_MONGOCRYPT_DEFAULT);
+
+    /* Ensure KMS encrypt requests retry for network errors */
+    ctx = mongocrypt_ctx_new(crypt);
+    ASSERT_OK(mongocrypt_ctx_rewrap_many_datakey_init(ctx, filter), ctx);
+    ASSERT_STATE_EQUAL(mongocrypt_ctx_state(ctx), MONGOCRYPT_CTX_NEED_MONGO_KEYS);
+    ASSERT_OK(mongocrypt_ctx_mongo_feed(ctx, TEST_FILE("./test/data/rmd/key-document-a.json")), ctx);
+    ASSERT_OK(mongocrypt_ctx_mongo_done(ctx), ctx);
+    ASSERT_STATE_EQUAL(mongocrypt_ctx_state(ctx), MONGOCRYPT_CTX_NEED_KMS); // To decrypt.
+    ASSERT((kms = mongocrypt_ctx_next_kms_ctx(ctx)));
+    ASSERT_OK(mongocrypt_kms_ctx_feed(kms, TEST_FILE("./test/data/rmd/kms-decrypt-reply-a.txt")), kms);
+    ASSERT(mongocrypt_kms_ctx_bytes_needed(kms) == 0);
+    ASSERT_OK(mongocrypt_ctx_kms_done(ctx), ctx);
+    ASSERT_STATE_EQUAL(mongocrypt_ctx_state(ctx), MONGOCRYPT_CTX_NEED_KMS); // To encrypt.
+    ASSERT((kms = mongocrypt_ctx_next_kms_ctx(ctx)));
+    ASSERT(mongocrypt_kms_ctx_fail(kms));             // Simulate driver-side network failure for an encrypt request.
+    ASSERT((kms = mongocrypt_ctx_next_kms_ctx(ctx))); // Assert fails. Expected KMS request to retry but did not.
+    ASSERT_OK(mongocrypt_kms_ctx_feed(kms, TEST_FILE("./test/data/rmd/kms-encrypt-reply-a.txt")), kms);
+    ASSERT(mongocrypt_kms_ctx_bytes_needed(kms) == 0);
+    ASSERT_OK(!mongocrypt_ctx_next_kms_ctx(ctx), ctx);
+    ASSERT_OK(mongocrypt_ctx_kms_done(ctx), ctx);
+    ASSERT_STATE_EQUAL(mongocrypt_ctx_state(ctx), MONGOCRYPT_CTX_READY);
+
     mongocrypt_ctx_destroy(ctx);
     mongocrypt_destroy(crypt);
 }