diff --git a/db/hints/manager.cc b/db/hints/manager.cc
index 4503a34130..cef7326c8f 100644
--- a/db/hints/manager.cc
+++ b/db/hints/manager.cc
@@ -758,8 +758,9 @@ future<> manager::end_point_hints_manager::sender::send_one_mutation(frozen_muta
 }
 
 future<> manager::end_point_hints_manager::sender::send_one_hint(lw_shared_ptr<send_one_file_ctx> ctx_ptr, fragmented_temporary_buffer buf, db::replay_position rp, gc_clock::duration secs_since_file_mod, const sstring& fname) {
-    ctx_ptr->last_attempted_rp = rp;
     return _resource_manager.get_send_units_for(buf.size_bytes()).then([this, secs_since_file_mod, &fname, buf = std::move(buf), rp, ctx_ptr] (auto units) mutable {
+        ctx_ptr->mark_hint_as_in_progress(rp);
+
         // Future is waited on indirectly in `send_one_file()` (via `ctx_ptr->file_send_gate`).
         (void)with_gate(ctx_ptr->file_send_gate, [this, secs_since_file_mod, &fname, buf = std::move(buf), rp, ctx_ptr] () mutable {
             try {
@@ -778,7 +779,7 @@ future<> manager::end_point_hints_manager::sender::send_one_hint(lw_shared_ptr<s
                     ++this->shard_stats().sent;
                 }).handle_exception([this, ctx_ptr, rp] (auto eptr) {
                     manager_logger.trace("send_one_hint(): failed to send to {}: {}", end_point_key(), eptr);
-                    ctx_ptr->on_hint_send_failure(rp);
+                    return make_exception_future<>(std::move(eptr));
                 });
 
             // ignore these errors and move on - probably this hint is too old and the KS/CF has been deleted...
@@ -792,17 +793,34 @@ future<> manager::end_point_hints_manager::sender::send_one_hint(lw_shared_ptr<s
                 manager_logger.debug("send_hints(): {} at {}: {}", fname, rp, e.what());
                 ++this->shard_stats().discarded;
             } catch (...) {
-                manager_logger.debug("send_hints(): unexpected error in file {} at {}: {}", fname, rp, std::current_exception());
-                ctx_ptr->on_hint_send_failure(rp);
+                auto eptr = std::current_exception();
+                manager_logger.debug("send_hints(): unexpected error in file {} at {}: {}", fname, rp, eptr);
+                return make_exception_future<>(std::move(eptr));
             }
             return make_ready_future<>();
-        }).finally([units = std::move(units), ctx_ptr] {});
+        }).then_wrapped([units = std::move(units), ctx_ptr, rp] (future<>&& f) {
+            // Information about the error was already printed somewhere higher.
+            // We just need to account in the ctx that sending of this hint has failed.
+            if (!f.failed()) {
+                ctx_ptr->on_hint_send_success(rp);
+            } else {
+                ctx_ptr->on_hint_send_failure(rp);
+            }
+            f.ignore_ready_future();
+        });
     }).handle_exception([this, ctx_ptr, rp] (auto eptr) {
         manager_logger.trace("send_one_file(): Hmmm. Something bad had happend: {}", eptr);
         ctx_ptr->on_hint_send_failure(rp);
     });
 }
 
+void manager::end_point_hints_manager::sender::send_one_file_ctx::mark_hint_as_in_progress(db::replay_position rp) {
+    last_attempted_rp = rp;
+}
+
+void manager::end_point_hints_manager::sender::send_one_file_ctx::on_hint_send_success(db::replay_position rp) noexcept {
+}
+
 void manager::end_point_hints_manager::sender::send_one_file_ctx::on_hint_send_failure(db::replay_position rp) noexcept {
     segment_replay_failed = true;
     if (!first_failed_rp || rp < *first_failed_rp) {
diff --git a/db/hints/manager.hh b/db/hints/manager.hh
index ef6004a770..2bae9cbb32 100644
--- a/db/hints/manager.hh
+++ b/db/hints/manager.hh
@@ -126,6 +126,8 @@ public:
                 std::optional<db::replay_position> last_attempted_rp;
                 bool segment_replay_failed = false;
 
+                void mark_hint_as_in_progress(db::replay_position rp);
+                void on_hint_send_success(db::replay_position rp) noexcept;
                 void on_hint_send_failure(db::replay_position rp) noexcept;
             };