diff --git a/extension/llm/custom_ops/op_sdpa.cpp b/extension/llm/custom_ops/op_sdpa.cpp
index 371fcf38a24..89634574027 100644
--- a/extension/llm/custom_ops/op_sdpa.cpp
+++ b/extension/llm/custom_ops/op_sdpa.cpp
@@ -382,7 +382,7 @@ void cpu_flash_attention(
       /* qk_sum */ qSplitSize +
       /* dst    */ qSplitSize * headSize;
 
-  int64_t size_bytes = size_per_thread * num_thread * query.element_size();
+  int64_t size_bytes = size_per_thread * num_thread * query.element_size() * 4;
   std::vector<char> buf_vec(size_bytes);
   void* buf = reinterpret_cast<void*>(buf_vec.data());
   // Need to double check the following
@@ -452,6 +452,7 @@ void cpu_flash_attention(
       // However, lets just fix that as well.
       int64_t num_keys =
           is_causal ? std::min(m + start_pos + qBlockSize, kvSize) : kvSize;
+      int64_t m_start_pos = m + start_pos;
       auto j_kv = j / num_reps;
       for (int64_t n = 0; n < num_keys; n += kvSplitSize) {
         int64_t kvBlockSize = std::min(kvSplitSize, kvSize - n);
@@ -471,29 +472,62 @@ void cpu_flash_attention(
             static_cast<accum_t>(0),
             qk_data,
             kvBlockSize);
-        // Apply causal mask, fill unused, i.e. future values, with -inf
-        // Say you have q @ k.T size = [16, 32]
-        // With qblock size = 4, say you are processing
-        // q seq len dim = 8:11.
-        // Say kvSplitSize = 4
-        // Then for causal mask, the entries that needs to be
-        // ignored are
-        // [8, 9:31], [9, 10:31], [10, 10:31], [11, 11:31]
-        // Following condition says that num_keys = 8 + 4 =12
-        // (num_keys - n) <= kvSplitSize
-        // num_keys <= n + kvSplitSize
-        // If n + kvSplitSize is larger than 12, then some
-        // entries need masked out. In our example n = 4
-        // will qualify for that
-        if (is_causal && num_keys - n <= kvSplitSize) {
+        // There are 4 cases that is_causal has to cover to fill
+        // not-attendable-position with -inf
+        /* 1. Everything is attended to. This happens when m_start_pos > n +
+        kvSplitSize e.g m_pos [8:15] and n_pos [0:7]. Since you must attend to
+        all previous tokens matrix is full
+        + + + + + + + +
+        + + + + + + + +
+        + + + + + + + +
+        + + + + + + + +
+        + + + + + + + +
+        + + + + + + + +
+        + + + + + + + +
+           2. Everything is not attended to. However only some tokens at the
+        beginning dont attend to everything. This happens when m_start_pos <= n
+        + kvSplitSize but m_start_pos + qBlockSize > n + kvSplitSize m_start_pos
+        = 8 qBlockSize = 8 n = 4 kvSplitSize = 8 For example m_pos [8:15] but
+        n_pos is [4:11]
+        + + + + + - - -
+        + + + + + + - -
+        + + + + + + + -
+        + + + + + + + +
+        + + + + + + + +
+        + + + + + + + +
+        + + + + + + + +
+        + + + + + + + +
+           3. In this case only last few tokens have something to attend to.
+        This happens when m_start_pos < n and m_start_pos + qBlockSize >= n and
+        m_start_pos + qBlockSize <= n + kvSplitSize m_start_pos = 8 qBlockSize =
+        8 n = 13 kvSplitSize = 8 For example m_pos [8:15] but n_pos is [13:20]
+        - - - - - - - -
+        - - - - - - - -
+        - - - - - - - -
+        - - - - - - - -
+        - - - - - - - -
+        + - - - - - - -
+        + + - - - - - -
+        + + + - - - - -
+           4. In this no tokens attend to anything, but we dont really have to
+        take care of this case because the loop for (int64_t n = 0; n <
+        num_keys; n += kvSplitSize) will exit before that.
+        */
+        if (is_causal && m_start_pos <= n + kvSplitSize) {
           // For this fn to work k_split_size > q_split_size
-          for (int32_t row = 0; row < qBlockSize; ++row) {
-            int64_t last_col = m + (row + start_pos) - n;
+          for (int32_t row = 0;
+               row < qBlockSize && (m_start_pos + row < n + (kvSplitSize - 1));
+               ++row) {
+            // When last_col is 0, it means that the entire row is not attended
+            // to because m_pos is smaller than n_pos. So everything in n is for
+            // future.
+            int64_t last_col =
+                n > (m_start_pos + row) ? 0 : row + m_start_pos + 1 - n;
             accum_t* row_ptr = qk_data + row * kvBlockSize;
             fill_stub(
-                row_ptr + last_col + 1,
+                row_ptr + last_col,
                 -std::numeric_limits<accum_t>::infinity(),
-                kvBlockSize - last_col - 1);
+                kvBlockSize - last_col);
           }
         }
         // Update attention weights with attention mask
diff --git a/extension/llm/custom_ops/test_sdpa_with_kv_cache.py b/extension/llm/custom_ops/test_sdpa_with_kv_cache.py
index 9c8029c7b70..a1f054a153e 100644
--- a/extension/llm/custom_ops/test_sdpa_with_kv_cache.py
+++ b/extension/llm/custom_ops/test_sdpa_with_kv_cache.py
@@ -590,3 +590,14 @@ def test_sdpa_with_cache_seq_len_llava_example_gqa(self):
         self._test_sdpa_common(
             n_heads_kv, n_heads_q, head_dim, max_seq_len, seq_len, next_iter_seq_len
         )
+
+    def test_sdpa_to_repro_long_seq_failure(self):
+        n_heads_kv = 16
+        n_heads_q = 32
+        head_dim = 128
+        max_seq_len = 2048
+        seq_len = 508
+        next_iter_seq_len = 127
+        self._test_sdpa_common(
+            n_heads_kv, n_heads_q, head_dim, max_seq_len, seq_len, next_iter_seq_len
+        )