diff --git a/fs/btrfs/block-group.c b/fs/btrfs/block-group.c
index 63c3b7172ba54..1e4b70f5280d8 100644
--- a/fs/btrfs/block-group.c
+++ b/fs/btrfs/block-group.c
@@ -441,13 +441,23 @@ void btrfs_wait_block_group_cache_progress(struct btrfs_block_group *cache,
 					   u64 num_bytes)
 {
 	struct btrfs_caching_control *caching_ctl;
+	int progress;
 
 	caching_ctl = btrfs_get_caching_control(cache);
 	if (!caching_ctl)
 		return;
 
+	/*
+	 * We've already failed to allocate from this block group, so even if
+	 * there's enough space in the block group it isn't contiguous enough to
+	 * allow for an allocation, so wait for at least the next wakeup tick,
+	 * or for the thing to be done.
+	 */
+	progress = atomic_read(&caching_ctl->progress);
+
 	wait_event(caching_ctl->wait, btrfs_block_group_done(cache) ||
-		   (cache->free_space_ctl->free_space >= num_bytes));
+		   (progress != atomic_read(&caching_ctl->progress) &&
+		    (cache->free_space_ctl->free_space >= num_bytes)));
 
 	btrfs_put_caching_control(caching_ctl);
 }
@@ -802,8 +812,10 @@ static int load_extent_tree_free(struct btrfs_caching_control *caching_ctl)
 
 			if (total_found > CACHING_CTL_WAKE_UP) {
 				total_found = 0;
-				if (wakeup)
+				if (wakeup) {
+					atomic_inc(&caching_ctl->progress);
 					wake_up(&caching_ctl->wait);
+				}
 			}
 		}
 		path->slots[0]++;
@@ -910,6 +922,7 @@ int btrfs_cache_block_group(struct btrfs_block_group *cache, bool wait)
 	init_waitqueue_head(&caching_ctl->wait);
 	caching_ctl->block_group = cache;
 	refcount_set(&caching_ctl->count, 2);
+	atomic_set(&caching_ctl->progress, 0);
 	btrfs_init_work(&caching_ctl->work, caching_thread, NULL, NULL);
 
 	spin_lock(&cache->lock);
diff --git a/fs/btrfs/block-group.h b/fs/btrfs/block-group.h
index aba5dff66c19f..74b61e663028a 100644
--- a/fs/btrfs/block-group.h
+++ b/fs/btrfs/block-group.h
@@ -90,6 +90,8 @@ struct btrfs_caching_control {
 	wait_queue_head_t wait;
 	struct btrfs_work work;
 	struct btrfs_block_group *block_group;
+	/* Track progress of caching during allocation. */
+	atomic_t progress;
 	refcount_t count;
 };