diff --git a/bindings/python/CHANGELOG.md b/bindings/python/CHANGELOG.md
index 577925bc..344e8df8 100644
--- a/bindings/python/CHANGELOG.md
+++ b/bindings/python/CHANGELOG.md
@@ -4,6 +4,7 @@ Fixes:
 - Some default tokens were missing from `BertWordPieceTokenizer` (cf [#160](https://github.com/huggingface/tokenizers/issues/160))
 - There was a bug in ByteLevel PreTokenizer that caused offsets to be wrong if a char got split up
 in multiple bytes. (cf [#156](https://github.com/huggingface/tokenizers/pull/156))
+- The `longest_first` truncation strategy had a bug ([#174](https://github.com/huggingface/tokenizers/issues/174))
 
 # v0.5.2
 - Do not open all files directly while training ([#163](https://github.com/huggingface/tokenizers/issues/163))
diff --git a/tokenizers/CHANGELOG.md b/tokenizers/CHANGELOG.md
index e1fea14b..b0f29a84 100644
--- a/tokenizers/CHANGELOG.md
+++ b/tokenizers/CHANGELOG.md
@@ -4,3 +4,4 @@
 - Do not open all files directly while training ([#163](https://github.com/huggingface/tokenizers/issues/163))
 - There was a bug in ByteLevel PreTokenizer that caused offsets to be wrong if a char got split up
 in multiple bytes. (cf [#156](https://github.com/huggingface/tokenizers/pull/156))
+- The `LongestFirst` truncation strategy had a bug ([#174](https://github.com/huggingface/tokenizers/issues/174))
diff --git a/tokenizers/src/tokenizer/encoding.rs b/tokenizers/src/tokenizer/encoding.rs
index 8ee58fee..c9a29e0c 100644
--- a/tokenizers/src/tokenizer/encoding.rs
+++ b/tokenizers/src/tokenizer/encoding.rs
@@ -91,11 +91,13 @@ impl Encoding {
 
     /// Truncate the current `Encoding`.
     ///
-    /// Panic if `stride >= max_len`.
+    /// Panic if `stride >= max_len` or `max_len == 0`.
     pub fn truncate(&mut self, max_len: usize, stride: usize) {
         if max_len >= self.ids.len() {
             return;
         }
+        // We only truncate if max_len > 0, it makes no sense otherwise
+        assert!(max_len > 0);
 
         // Get the main overflowing part
         let o_ids = self.ids.split_off(max_len);
@@ -105,7 +107,7 @@ impl Encoding {
         let o_spe_toks = self.special_tokens_mask.split_off(max_len);
         let o_attent = self.attention_mask.split_off(max_len);
 
-        // Now we need to separate each overflowing part into as many Encoding as needed
+        // Now we need to separate the overflowing part into as many Encoding as needed
         assert!(stride < max_len);
         let part_size = max_len - stride;
         let mut overflowing = vec![];
diff --git a/tokenizers/src/utils.rs b/tokenizers/src/utils.rs
index 2a8c187a..efc3ca5e 100644
--- a/tokenizers/src/utils.rs
+++ b/tokenizers/src/utils.rs
@@ -83,21 +83,19 @@ pub fn truncate_encodings(
 
     match params.strategy {
         TruncationStrategy::LongestFirst => {
-            let mut n_first = 0;
-            let mut n_second = 0;
+            let mut n_first = encoding.get_ids().len();
+            let mut n_second = pair_encoding.as_ref().map_or(0, |e| e.get_ids().len());
             for _ in 0..to_remove {
-                if pair_encoding.is_none()
-                    || encoding.get_ids().len() > pair_encoding.as_ref().unwrap().get_ids().len()
-                {
-                    n_first += 1;
+                if n_first > n_second {
+                    n_first -= 1;
                 } else {
-                    n_second += 1;
+                    n_second -= 1;
                 }
             }
 
-            encoding.truncate(encoding.get_ids().len() - n_first, params.stride);
+            encoding.truncate(n_first, params.stride);
             if let Some(encoding) = pair_encoding.as_mut() {
-                encoding.truncate(encoding.get_ids().len() - n_second, params.stride);
+                encoding.truncate(n_second, params.stride);
             }
         }
         TruncationStrategy::OnlyFirst | TruncationStrategy::OnlySecond => {