diff --git a/ddtrace/appsec/_iast/_patch.py b/ddtrace/appsec/_iast/_patch.py
index d6d8fefce08..268514b24ce 100644
--- a/ddtrace/appsec/_iast/_patch.py
+++ b/ddtrace/appsec/_iast/_patch.py
@@ -166,11 +166,13 @@ def if_iast_taint_yield_tuple_for(origins, wrapped, instance, args, kwargs):
         if not AppSecIastSpanProcessor.is_span_analyzed():
             for key, value in wrapped(*args, **kwargs):
                 yield key, value
-
-        for key, value in wrapped(*args, **kwargs):
-            new_key = taint_pyobject(pyobject=key, source_name=key, source_value=key, source_origin=origins[0])
-            new_value = taint_pyobject(pyobject=value, source_name=key, source_value=value, source_origin=origins[1])
-            yield new_key, new_value
+        else:
+            for key, value in wrapped(*args, **kwargs):
+                new_key = taint_pyobject(pyobject=key, source_name=key, source_value=key, source_origin=origins[0])
+                new_value = taint_pyobject(
+                    pyobject=value, source_name=key, source_value=value, source_origin=origins[1]
+                )
+                yield new_key, new_value
 
     else:
         for key, value in wrapped(*args, **kwargs):
diff --git a/releasenotes/notes/iast-fix-flask-duplicated-headers-565e6d8ebb75a883.yaml b/releasenotes/notes/iast-fix-flask-duplicated-headers-565e6d8ebb75a883.yaml
new file mode 100644
index 00000000000..4ecc76e6504
--- /dev/null
+++ b/releasenotes/notes/iast-fix-flask-duplicated-headers-565e6d8ebb75a883.yaml
@@ -0,0 +1,5 @@
+---
+fixes:
+  - |
+    Code Security: Ensure that when tainting the headers of a Flask application, iterating over the headers 
+    (i.e., with `headers.items()`) does not duplicate them.
\ No newline at end of file
diff --git a/tests/appsec/iast_tdd_propagation/flask_propagation_app.py b/tests/appsec/iast_tdd_propagation/flask_propagation_app.py
new file mode 100644
index 00000000000..1c1b23f9fbb
--- /dev/null
+++ b/tests/appsec/iast_tdd_propagation/flask_propagation_app.py
@@ -0,0 +1,9 @@
+from flask_propagation_views import create_app
+
+from ddtrace import auto  # noqa: F401
+
+
+app = create_app()
+
+if __name__ == "__main__":
+    app.run(debug=False, port=8000)
diff --git a/tests/appsec/iast_tdd_propagation/flask_propagation_views.py b/tests/appsec/iast_tdd_propagation/flask_propagation_views.py
new file mode 100644
index 00000000000..0cf9f201d7f
--- /dev/null
+++ b/tests/appsec/iast_tdd_propagation/flask_propagation_views.py
@@ -0,0 +1,47 @@
+import sys
+
+from flask import Flask
+from flask import request
+
+from ddtrace import tracer
+from ddtrace.appsec._iast._taint_tracking import is_pyobject_tainted
+
+
+class ResultResponse:
+    param = ""
+    sources = ""
+    vulnerabilities = ""
+
+    def __init__(self, param):
+        self.param = param
+
+    def json(self):
+        return {
+            "param": self.param,
+            "sources": self.sources,
+            "vulnerabilities": self.vulnerabilities,
+            "params_are_tainted": is_pyobject_tainted(self.param),
+        }
+
+
+def create_app():
+    app = Flask(__name__)
+
+    @app.route("/shutdown")
+    def shutdown():
+        tracer.shutdown()
+        sys.exit(0)
+
+    @app.route("/")
+    def index():
+        return "OK"
+
+    @app.route("/check-headers")
+    def check_headers():
+        headers = list(request.headers.items())
+
+        response = ResultResponse(headers)
+
+        return response.json()
+
+    return app
diff --git a/tests/appsec/iast_tdd_propagation/flask_taint_sinks_app.py b/tests/appsec/iast_tdd_propagation/flask_taint_sinks_app.py
index be5773a1490..b140a953812 100644
--- a/tests/appsec/iast_tdd_propagation/flask_taint_sinks_app.py
+++ b/tests/appsec/iast_tdd_propagation/flask_taint_sinks_app.py
@@ -1,7 +1,3 @@
-#!/usr/bin/env python3
-
-""" This Flask application is imported on tests.appsec.appsec_utils.gunicorn_server
-"""
 from flask_taint_sinks_views import create_app
 
 from ddtrace import auto  # noqa: F401
diff --git a/tests/appsec/iast_tdd_propagation/test_flask.py b/tests/appsec/iast_tdd_propagation/test_flask.py
index 6618f7f684f..b3526a6325d 100644
--- a/tests/appsec/iast_tdd_propagation/test_flask.py
+++ b/tests/appsec/iast_tdd_propagation/test_flask.py
@@ -52,6 +52,7 @@ def test_iast_flask_orm(orm, xfail):
 
 
 def test_iast_flask_weak_cipher():
+    """Verify a segmentation fault on pycriptodome and AES"""
     with flask_server(
         iast_enabled="true",
         tracer_enabled="true",
@@ -83,3 +84,26 @@ def test_iast_flask_weak_cipher():
             assert content["sources"] == ""
             assert content["vulnerabilities"] == "WEAK_CIPHER"
             assert content["params_are_tainted"] is True
+
+
+def test_iast_flask_headers():
+    """Verify duplicated headers in the request"""
+    with flask_server(
+        iast_enabled="true",
+        tracer_enabled="true",
+        remote_configuration_enabled="false",
+        token=None,
+        app="tests/appsec/iast_tdd_propagation/flask_propagation_app.py",
+    ) as context:
+        server_process, client, pid = context
+        tainted_response = client.get("/check-headers", headers={"Accept-Encoding": "gzip, deflate, br"})
+
+        assert tainted_response.status_code == 200
+        content = json.loads(tainted_response.content)
+        assert content["param"] == [
+            ["Host", "0.0.0.0:8000"],
+            ["User-Agent", "python-requests/2.31.0"],
+            ["Accept-Encoding", "gzip, deflate, br"],
+            ["Accept", "*/*"],
+            ["Connection", "keep-alive"],
+        ]