diff --git a/boudams/cli.py b/boudams/cli.py
index b46b51b..46c7811 100644
--- a/boudams/cli.py
+++ b/boudams/cli.py
@@ -413,14 +413,19 @@ def tag(model, filename, device="cpu", batch_size=64):
     print("Model loaded.")
     for file in tqdm.tqdm(filename):
         out_name = file.name.replace(".txt", ".tokenized.txt")
-        with open(file) as f, open(out_name, "w") as out_io:
-            content = f.read()  # Could definitely be done a better way...
-            if model.vocabulary.mode.name == "simple-space":
-                content = re.sub(r"\s+", "", content)
-            elif model.vocabulary.mode.NormalizeSpace:
-                content = re.sub(r"\s+", " ", content)
+        content = file.read()  # Could definitely be done a better way...
+        if model.vocabulary.mode.name == "simple-space":
+            content = re.sub(r"\s+", "", content)
+        elif model.vocabulary.mode.NormalizeSpace:
+            content = re.sub(r"\s+", " ", content)
+        file.close()
+        with open(out_name, "w") as out_io:
             out = ''
-            for tokenized_string in model.annotate_text(content, batch_size=batch_size, device=device):
+            for tokenized_string in model.annotate_text(
+                    content,
+                    batch_size=batch_size,
+                    device=device
+            ):
                 out = out + tokenized_string + "\n"
             out_io.write(out)
         print("--- File " + file.name + " has been tokenized")
@@ -438,7 +443,7 @@ def tag_check(config_model, content, device="cpu", batch_size=64):
         boudams = BoudamsTagger.load(model, device=device)
         boudams.eval()
         click.echo(f"\t[X] Model loaded")
-        click.echo("\n".join(boudams.annotate_text(content, splitter="([\.!\?]+)", batch_size=batch_size, device=device)))
+        click.echo("\n".join(boudams.annotate_text(content, splitter=r"([\.!\?]+)", batch_size=batch_size, device=device)))
 
 
 @cli.command("graph")
diff --git a/boudams/tagger.py b/boudams/tagger.py
index 7f30845..51f2aad 100644
--- a/boudams/tagger.py
+++ b/boudams/tagger.py
@@ -449,27 +449,47 @@ def annotate(self, texts: List[str], batch_size=32, device: str = "cpu"):
             for index in range(len(translations)):
                 yield "".join(translations[order.index(index)])
 
-    def annotate_text(self, string, splitter=r"([⁊\W\d]+)", batch_size=32, device: str = "cpu"):
-        splitter = re.compile(splitter)
-        splits = splitter.split(string)
-
-        tempList = splits + [""] * 2
-        strings = ["".join(tempList[n:n + 2]) for n in range(0, len(splits), 2)]
-        strings = list(filter(lambda x: x.strip(), strings))
+    @staticmethod
+    def _apply_max_size(tokens: str, size: int):
+        # Use finditer when applied to things with spaces ?
+        #  [(m.start(0), m.end(0)) for m in re.finditer(pattern, string)] ?
+        current = []
+        for tok in re.split(r"(\s+)", tokens):
+            if not tok:
+                continue
+            current.append(tok)
+            string_size = len("".join(current))
+            if string_size > size:
+                yield "".join(current[:-1])
+                current = current[-1:]
+            elif string_size == size:
+                yield "".join(current)
+                current = []
+        if current:
+            yield "".join(current)
+
+    def annotate_text(self, single_sentence, splitter: Optional[str] = None, batch_size=32, device: str = "cpu", rolling=True):
+        if splitter is None:
+            # ToDo: Mode specific splitter ?
+            splitter = r"([\.!\?]+)"
 
+        splitter = re.compile(splitter)
+        sentences = [tok for tok in splitter.split(single_sentence) if tok.strip()]
+                
         if self._maximum_sentence_size:
+            # This is currently quite limitating.
+            # If the end token is ending with a W and not a WB, there is no way to "correct it"
+            # We'd need a rolling system: cut in the middle of maximum sentence size ?
             treated = []
             max_size = self._maximum_sentence_size
-            for string in strings:
-                if len(string) > max_size:
-                    treated.extend([
-                        "".join(string[n:n + max_size])
-                        for n in range(0, len(string), max_size)
-                    ])
+            for single_sentence in sentences:
+                if len(single_sentence) > max_size:
+                    treated.extend(self._apply_max_size(single_sentence, max_size))
                 else:
-                    treated.append(string)
-            strings = treated
-        yield from self.annotate(strings, batch_size=batch_size, device=device)
+                    treated.append(single_sentence)
+            sentences = treated
+
+        yield from self.annotate(sentences, batch_size=batch_size, device=device)
 
     @classmethod
     def load(cls, fpath="./model.boudams_model", device=None):