diff --git a/features/filesystem/littlefs/littlefs/lfs.c b/features/filesystem/littlefs/littlefs/lfs.c
index 3ba8b3b708..0ae983d573 100644
--- a/features/filesystem/littlefs/littlefs/lfs.c
+++ b/features/filesystem/littlefs/littlefs/lfs.c
@@ -270,8 +270,7 @@ int lfs_deorphan(lfs_t *lfs);
 static int lfs_alloc_lookahead(void *p, lfs_block_t block) {
     lfs_t *lfs = p;
 
-    lfs_block_t off = (((lfs_soff_t)(block - lfs->free.begin)
-                % (lfs_soff_t)(lfs->cfg->block_count))
+    lfs_block_t off = ((block - lfs->free.off)
             + lfs->cfg->block_count) % lfs->cfg->block_count;
 
     if (off < lfs->free.size) {
@@ -283,27 +282,38 @@ static int lfs_alloc_lookahead(void *p, lfs_block_t block) {
 
 static int lfs_alloc(lfs_t *lfs, lfs_block_t *block) {
     while (true) {
-        while (lfs->free.off != lfs->free.size) {
-            lfs_block_t off = lfs->free.off;
-            lfs->free.off += 1;
+        while (lfs->free.index != lfs->free.size) {
+            lfs_block_t off = lfs->free.index;
+            lfs->free.index += 1;
+            lfs->free.ack -= 1;
 
             if (!(lfs->free.buffer[off / 32] & (1U << (off % 32)))) {
                 // found a free block
-                *block = (lfs->free.begin + off) % lfs->cfg->block_count;
+                *block = (lfs->free.off + off) % lfs->cfg->block_count;
+
+                // eagerly find next off so an alloc ack can
+                // discredit old lookahead blocks
+                while (lfs->free.index != lfs->free.size &&
+                        (lfs->free.buffer[lfs->free.index / 32]
+                            & (1U << (lfs->free.index % 32)))) {
+                    lfs->free.index += 1;
+                    lfs->free.ack -= 1;
+                }
+
                 return 0;
             }
         }
 
         // check if we have looked at all blocks since last ack
-        if (lfs->free.off == lfs->free.ack - lfs->free.begin) {
-            LFS_WARN("No more free space %ld", lfs->free.off + lfs->free.begin);
+        if (lfs->free.ack == 0) {
+            LFS_WARN("No more free space %ld", lfs->free.index+lfs->free.off);
             return LFS_ERR_NOSPC;
         }
 
-        lfs->free.begin += lfs->free.size;
-        lfs->free.size = lfs_min(lfs->cfg->lookahead,
-                lfs->free.ack - lfs->free.begin);
-        lfs->free.off = 0;
+        lfs->free.off = (lfs->free.off + lfs->free.size)
+                % lfs->cfg->block_count;
+        lfs->free.size = lfs_min(lfs->cfg->lookahead, lfs->free.ack);
+        lfs->free.index = 0;
 
         // find mask of free blocks from tree
         memset(lfs->free.buffer, 0, lfs->cfg->lookahead/8);
@@ -315,7 +325,7 @@ static int lfs_alloc(lfs_t *lfs, lfs_block_t *block) {
 }
 
 static void lfs_alloc_ack(lfs_t *lfs) {
-    lfs->free.ack = lfs->free.off-1 + lfs->free.begin + lfs->cfg->block_count;
+    lfs->free.ack = lfs->cfg->block_count;
 }
 
 
@@ -2094,9 +2104,9 @@ int lfs_format(lfs_t *lfs, const struct lfs_config *cfg) {
 
     // create free lookahead
     memset(lfs->free.buffer, 0, lfs->cfg->lookahead/8);
-    lfs->free.begin = 0;
-    lfs->free.size = lfs_min(lfs->cfg->lookahead, lfs->cfg->block_count);
     lfs->free.off = 0;
+    lfs->free.size = lfs_min(lfs->cfg->lookahead, lfs->cfg->block_count);
+    lfs->free.index = 0;
     lfs_alloc_ack(lfs);
 
     // create superblock dir
@@ -2173,9 +2183,9 @@ int lfs_mount(lfs_t *lfs, const struct lfs_config *cfg) {
     }
 
     // setup free lookahead
-    lfs->free.begin = 0;
-    lfs->free.size = 0;
     lfs->free.off = 0;
+    lfs->free.size = 0;
+    lfs->free.index = 0;
     lfs_alloc_ack(lfs);
 
     // load superblock
diff --git a/features/filesystem/littlefs/littlefs/lfs.h b/features/filesystem/littlefs/littlefs/lfs.h
index f20a1d4f00..68310f1542 100644
--- a/features/filesystem/littlefs/littlefs/lfs.h
+++ b/features/filesystem/littlefs/littlefs/lfs.h
@@ -259,9 +259,9 @@ typedef struct lfs_superblock {
 } lfs_superblock_t;
 
 typedef struct lfs_free {
-    lfs_block_t begin;
-    lfs_block_t size;
     lfs_block_t off;
+    lfs_block_t size;
+    lfs_block_t index;
     lfs_block_t ack;
     uint32_t *buffer;
 } lfs_free_t;
diff --git a/features/filesystem/littlefs/littlefs/tests/test_alloc.sh b/features/filesystem/littlefs/littlefs/tests/test_alloc.sh
index 493270d103..8c814908b5 100755
--- a/features/filesystem/littlefs/littlefs/tests/test_alloc.sh
+++ b/features/filesystem/littlefs/littlefs/tests/test_alloc.sh
@@ -289,7 +289,7 @@ tests/test.py << TEST
     }
     lfs_file_close(&lfs, &file[0]) => 0;
 
-    // open whole
+    // open hole
     lfs_remove(&lfs, "bump") => 0;
 
     lfs_mkdir(&lfs, "splitdir") => 0;
@@ -301,5 +301,128 @@ tests/test.py << TEST
     lfs_unmount(&lfs) => 0;
 TEST
 
+echo "--- Outdated lookahead test ---"
+rm -rf blocks
+tests/test.py << TEST
+    lfs_format(&lfs, &cfg) => 0;
+
+    lfs_mount(&lfs, &cfg) => 0;
+
+    // fill completely with two files
+    lfs_file_open(&lfs, &file[0], "exhaustion1",
+            LFS_O_WRONLY | LFS_O_CREAT) => 0;
+    size = strlen("blahblahblahblah");
+    memcpy(buffer, "blahblahblahblah", size);
+    for (lfs_size_t i = 0;
+            i < ((cfg.block_count-4)/2)*(cfg.block_size-8);
+            i += size) {
+        lfs_file_write(&lfs, &file[0], buffer, size) => size;
+    }
+    lfs_file_close(&lfs, &file[0]) => 0;
+
+    lfs_file_open(&lfs, &file[0], "exhaustion2",
+            LFS_O_WRONLY | LFS_O_CREAT) => 0;
+    size = strlen("blahblahblahblah");
+    memcpy(buffer, "blahblahblahblah", size);
+    for (lfs_size_t i = 0;
+            i < ((cfg.block_count-4+1)/2)*(cfg.block_size-8);
+            i += size) {
+        lfs_file_write(&lfs, &file[0], buffer, size) => size;
+    }
+    lfs_file_close(&lfs, &file[0]) => 0;
+
+    // remount to force reset of lookahead
+    lfs_unmount(&lfs) => 0;
+
+    lfs_mount(&lfs, &cfg) => 0;
+
+    // rewrite one file
+    lfs_file_open(&lfs, &file[0], "exhaustion1",
+            LFS_O_WRONLY | LFS_O_TRUNC) => 0;
+    lfs_file_sync(&lfs, &file[0]) => 0;
+    size = strlen("blahblahblahblah");
+    memcpy(buffer, "blahblahblahblah", size);
+    for (lfs_size_t i = 0;
+            i < ((cfg.block_count-4)/2)*(cfg.block_size-8);
+            i += size) {
+        lfs_file_write(&lfs, &file[0], buffer, size) => size;
+    }
+    lfs_file_close(&lfs, &file[0]) => 0;
+
+    // rewrite second file, this requires lookahead does not
+    // use old population
+    lfs_file_open(&lfs, &file[0], "exhaustion2",
+            LFS_O_WRONLY | LFS_O_TRUNC) => 0;
+    lfs_file_sync(&lfs, &file[0]) => 0;
+    size = strlen("blahblahblahblah");
+    memcpy(buffer, "blahblahblahblah", size);
+    for (lfs_size_t i = 0;
+            i < ((cfg.block_count-4+1)/2)*(cfg.block_size-8);
+            i += size) {
+        lfs_file_write(&lfs, &file[0], buffer, size) => size;
+    }
+    lfs_file_close(&lfs, &file[0]) => 0;
+TEST
+
+echo "--- Outdated lookahead and split dir test ---"
+rm -rf blocks
+tests/test.py << TEST
+    lfs_format(&lfs, &cfg) => 0;
+
+    lfs_mount(&lfs, &cfg) => 0;
+
+    // fill completely with two files
+    lfs_file_open(&lfs, &file[0], "exhaustion1",
+            LFS_O_WRONLY | LFS_O_CREAT) => 0;
+    size = strlen("blahblahblahblah");
+    memcpy(buffer, "blahblahblahblah", size);
+    for (lfs_size_t i = 0;
+            i < ((cfg.block_count-4)/2)*(cfg.block_size-8);
+            i += size) {
+        lfs_file_write(&lfs, &file[0], buffer, size) => size;
+    }
+    lfs_file_close(&lfs, &file[0]) => 0;
+
+    lfs_file_open(&lfs, &file[0], "exhaustion2",
+            LFS_O_WRONLY | LFS_O_CREAT) => 0;
+    size = strlen("blahblahblahblah");
+    memcpy(buffer, "blahblahblahblah", size);
+    for (lfs_size_t i = 0;
+            i < ((cfg.block_count-4+1)/2)*(cfg.block_size-8);
+            i += size) {
+        lfs_file_write(&lfs, &file[0], buffer, size) => size;
+    }
+    lfs_file_close(&lfs, &file[0]) => 0;
+
+    // remount to force reset of lookahead
+    lfs_unmount(&lfs) => 0;
+
+    lfs_mount(&lfs, &cfg) => 0;
+
+    // rewrite one file with a hole of one block
+    lfs_file_open(&lfs, &file[0], "exhaustion1",
+            LFS_O_WRONLY | LFS_O_TRUNC) => 0;
+    lfs_file_sync(&lfs, &file[0]) => 0;
+    size = strlen("blahblahblahblah");
+    memcpy(buffer, "blahblahblahblah", size);
+    for (lfs_size_t i = 0;
+            i < ((cfg.block_count-4)/2 - 1)*(cfg.block_size-8);
+            i += size) {
+        lfs_file_write(&lfs, &file[0], buffer, size) => size;
+    }
+    lfs_file_close(&lfs, &file[0]) => 0;
+
+    // try to allocate a directory, should fail!
+    lfs_mkdir(&lfs, "split") => LFS_ERR_NOSPC;
+
+    // file should not fail
+    lfs_file_open(&lfs, &file[0], "notasplit",
+            LFS_O_WRONLY | LFS_O_CREAT) => 0;
+    lfs_file_write(&lfs, &file[0], "hi", 2) => 2;
+    lfs_file_close(&lfs, &file[0]) => 0;
+
+    lfs_unmount(&lfs) => 0;
+TEST
+
 echo "--- Results ---"
 tests/stats.py