Implement support for multiple headers with the same name in sessions (#1335)

* Properly remove duplicate Cookie headers

* Implement support for multiple headers with the same name in sessions

* More testing

* Cleanup

* Remove duplicated test, cleanup

* Fix pycodestyle

* CHANGELOG

Co-authored-by: Jakub Roztocil <jakub@roztocil.co>

CHANGELOG.md

@@ -5,6 +5,7 @@ This project adheres to [Semantic Versioning](https://semver.org/).
 
 ## [3.1.1.dev0](https://github.com/httpie/httpie/compare/3.1.0...HEAD) (Unreleased)
 
+- Added support for session persistence of repeated headers with the same name. ([#1335](https://github.com/httpie/httpie/pull/1335))
 - Changed `httpie plugins` to the new `httpie cli` namespace as `httpie cli plugins` (`httpie plugins` continues to work as a hidden alias). ([#1320](https://github.com/httpie/httpie/issues/1320))
 - Fixed redundant creation of `Content-Length` header on `OPTIONS` requests. ([#1310](https://github.com/httpie/httpie/issues/1310))
 

httpie/cli/dicts.py

@@ -35,6 +35,16 @@ class HTTPHeadersDict(CIMultiDict, BaseMultiDict):
 
         super().add(key, value)
 
+    def remove_item(self, key, value):
+        """
+        Remove a (key, value) pair from the dict.
+        """
+        existing_values = self.popall(key)
+        existing_values.remove(value)
+
+        for value in existing_values:
+            self.add(key, value)
+
 
 class RequestJSONDataDict(OrderedDict):
     pass

httpie/legacy/v3_1_0_session_cookie_format.py

@@ -4,6 +4,7 @@ from typing import Any, Type, List, Dict, TYPE_CHECKING
 if TYPE_CHECKING:
     from httpie.sessions import Session
 
+
 INSECURE_COOKIE_JAR_WARNING = '''\
 Outdated layout detected for the current session. Please consider updating it,
 in order to not get affected by potential security problems.
@@ -53,16 +54,12 @@ def pre_process(session: 'Session', cookies: Any) -> List[Dict[str, Any]]:
         for cookie in normalized_cookies
     )
 
-    if should_issue_warning and not session.refactor_mode:
+    if should_issue_warning:
         warning = INSECURE_COOKIE_JAR_WARNING.format(hostname=session.bound_host, session_id=session.session_id)
         if not session.is_anonymous:
             warning += INSECURE_COOKIE_JAR_WARNING_FOR_NAMED_SESSIONS
         warning += INSECURE_COOKIE_SECURITY_LINK
-
+        session.warn_legacy_usage(warning)
-        session.env.log_error(
-            warning,
-            level='warning'
-        )
 
     return normalized_cookies
 

httpie/legacy/v3_2_0_session_header_format.py

@@ -0,0 +1,73 @@
+from typing import Any, Type, List, Dict, TYPE_CHECKING
+
+if TYPE_CHECKING:
+    from httpie.sessions import Session
+
+
+OLD_HEADER_STORE_WARNING = '''\
+Outdated layout detected for the current session. Please consider updating it,
+in order to use the latest features regarding the header layout.
+
+For fixing the current session:
+
+    $ httpie cli sessions upgrade {hostname} {session_id}
+'''
+
+OLD_HEADER_STORE_WARNING_FOR_NAMED_SESSIONS = '''\
+
+For fixing all named sessions:
+
+    $ httpie cli sessions upgrade-all
+'''
+
+OLD_HEADER_STORE_LINK = '\nSee $INSERT_LINK for more information.'
+
+
+def pre_process(session: 'Session', headers: Any) -> List[Dict[str, Any]]:
+    """Serialize the headers into a unified form and issue a warning if
+    the session file is using the old layout."""
+
+    is_old_style = isinstance(headers, dict)
+    if is_old_style:
+        normalized_headers = list(headers.items())
+    else:
+        normalized_headers = [
+            (item['name'], item['value'])
+            for item in headers
+        ]
+
+    if is_old_style:
+        warning = OLD_HEADER_STORE_WARNING.format(hostname=session.bound_host, session_id=session.session_id)
+        if not session.is_anonymous:
+            warning += OLD_HEADER_STORE_WARNING_FOR_NAMED_SESSIONS
+        warning += OLD_HEADER_STORE_LINK
+        session.warn_legacy_usage(warning)
+
+    return normalized_headers
+
+
+def post_process(
+    normalized_headers: List[Dict[str, Any]],
+    *,
+    original_type: Type[Any]
+) -> Any:
+    """Deserialize given header store into the original form it was
+    used in."""
+
+    if issubclass(original_type, dict):
+        # For the legacy behavior, preserve the last value.
+        return {
+            item['name']: item['value']
+            for item in normalized_headers
+        }
+    else:
+        return normalized_headers
+
+
+def fix_layout(session: 'Session', *args, **kwargs) -> None:
+    from httpie.sessions import materialize_headers
+
+    if not isinstance(session['headers'], dict):
+        return None
+
+    session['headers'] = materialize_headers(session['headers'])

httpie/manager/tasks/sessions.py

@@ -4,10 +4,16 @@ from typing import Tuple
 from httpie.sessions import SESSIONS_DIR_NAME, get_httpie_session
 from httpie.status import ExitStatus
 from httpie.context import Environment
-from httpie.legacy import cookie_format as legacy_cookies
+from httpie.legacy import v3_1_0_session_cookie_format, v3_2_0_session_header_format
 from httpie.manager.cli import missing_subcommand, parser
 
 
+FIXERS_TO_VERSIONS = {
+    '3.1.0': v3_1_0_session_cookie_format.fix_layout,
+    '3.2.0': v3_2_0_session_header_format.fix_layout,
+}
+
+
 def cli_sessions(env: Environment, args: argparse.Namespace) -> ExitStatus:
     action = args.cli_sessions_action
     if action is None:
@@ -22,7 +28,7 @@ def cli_sessions(env: Environment, args: argparse.Namespace) -> ExitStatus:
 
 
 def is_version_greater(version_1: str, version_2: str) -> bool:
-    # In an ideal scenerio, we would depend on `packaging` in order
+    # In an ideal scenario, we would depend on `packaging` in order
     # to offer PEP 440 compatible parsing. But since it might not be
     # commonly available for outside packages, and since we are only
     # going to parse HTTPie's own version it should be fine to compare
@@ -40,11 +46,6 @@ def is_version_greater(version_1: str, version_2: str) -> bool:
     return split_version(version_1) > split_version(version_2)
 
 
-FIXERS_TO_VERSIONS = {
-    '3.1.0': legacy_cookies.fix_layout
-}
-
-
 def upgrade_session(env: Environment, args: argparse.Namespace, hostname: str, session_name: str):
     session = get_httpie_session(
         env=env,
@@ -52,7 +53,7 @@ def upgrade_session(env: Environment, args: argparse.Namespace, hostname: str, s
         session_name=session_name,
         host=hostname,
         url=hostname,
-        refactor_mode=True
+        suppress_legacy_warnings=True
     )
 
     session_name = session.path.stem

httpie/sessions.py

@@ -13,12 +13,16 @@ from typing import Any, Dict, List, Optional, Union
 from requests.auth import AuthBase
 from requests.cookies import RequestsCookieJar, remove_cookie_by_name
 
-from .context import Environment
+from .context import Environment, Levels
 from .cli.dicts import HTTPHeadersDict
 from .config import BaseConfigDict, DEFAULT_CONFIG_DIR
 from .utils import url_as_host
 from .plugins.registry import plugin_manager
-from .legacy import cookie_format as legacy_cookies
+
+from .legacy import (
+    v3_1_0_session_cookie_format as legacy_cookies,
+    v3_2_0_session_header_format as legacy_headers
+)
 
 
 SESSIONS_DIR_NAME = 'sessions'
@@ -67,6 +71,23 @@ def materialize_cookie(cookie: Cookie) -> Dict[str, Any]:
     return materialized_cookie
 
 
+def materialize_cookies(jar: RequestsCookieJar) -> List[Dict[str, Any]]:
+    return [
+        materialize_cookie(cookie)
+        for cookie in jar
+    ]
+
+
+def materialize_headers(headers: Dict[str, str]) -> List[Dict[str, Any]]:
+    return [
+        {
+            'name': name,
+            'value': value
+        }
+        for name, value in headers.copy().items()
+    ]
+
+
 def get_httpie_session(
     env: Environment,
     config_dir: Path,
@@ -74,7 +95,7 @@ def get_httpie_session(
     host: Optional[str],
     url: str,
     *,
-    refactor_mode: bool = False
+    suppress_legacy_warnings: bool = False
 ) -> 'Session':
     bound_hostname = host or url_as_host(url)
     if not bound_hostname:
@@ -93,7 +114,7 @@ def get_httpie_session(
         env=env,
         session_id=session_id,
         bound_host=strip_port(bound_hostname),
-        refactor_mode=refactor_mode
+        suppress_legacy_warnings=suppress_legacy_warnings
     )
     session.load()
     return session
@@ -109,30 +130,29 @@ class Session(BaseConfigDict):
         env: Environment,
         bound_host: str,
         session_id: str,
-        refactor_mode: bool = False,
+        suppress_legacy_warnings: bool = False,
     ):
         super().__init__(path=Path(path))
-        self['headers'] = {}
+
+        # Default values for the session files
+        self['headers'] = []
         self['cookies'] = []
         self['auth'] = {
             'type': None,
             'username': None,
             'password': None
         }
+
+        # Runtime state of the Session objects.
         self.env = env
+        self._headers = HTTPHeadersDict()
         self.cookie_jar = RequestsCookieJar()
         self.session_id = session_id
         self.bound_host = bound_host
-        self.refactor_mode = refactor_mode
+        self.suppress_legacy_warnings = suppress_legacy_warnings
 
-    def pre_process_data(self, data: Dict[str, Any]) -> Dict[str, Any]:
+    def _add_cookies(self, cookies: List[Dict[str, Any]]) -> None:
-        cookies = data.get('cookies')
+        for cookie in cookies:
-        if cookies:
-            normalized_cookies = legacy_cookies.pre_process(self, cookies)
-        else:
-            normalized_cookies = []
-
-        for cookie in normalized_cookies:
             domain = cookie.get('domain', '')
             if domain is None:
                 # domain = None means explicitly lack of cookie, though
@@ -143,29 +163,38 @@ class Session(BaseConfigDict):
 
             self.cookie_jar.set(**cookie)
 
+    def pre_process_data(self, data: Dict[str, Any]) -> Dict[str, Any]:
+        for key, deserializer, importer in [
+            ('cookies', legacy_cookies.pre_process, self._add_cookies),
+            ('headers', legacy_headers.pre_process, self._headers.update),
+        ]:
+            values = data.get(key)
+            if values:
+                normalized_values = deserializer(self, values)
+            else:
+                normalized_values = []
+
+            importer(normalized_values)
+
         return data
 
     def post_process_data(self, data: Dict[str, Any]) -> Dict[str, Any]:
-        cookies = data.get('cookies')
+        for key, store, serializer, exporter in [
+            ('cookies', self.cookie_jar, materialize_cookies, legacy_cookies.post_process),
+            ('headers', self._headers, materialize_headers, legacy_headers.post_process),
+        ]:
+            original_type = type(data.get(key))
+            values = serializer(store)
 
-        normalized_cookies = [
+            data[key] = exporter(
-            materialize_cookie(cookie)
+                values,
-            for cookie in self.cookie_jar
+                original_type=original_type
-        ]
+            )
-        data['cookies'] = legacy_cookies.post_process(
-            normalized_cookies,
-            original_type=type(cookies)
-        )
 
         return data
 
-    def update_headers(self, request_headers: HTTPHeadersDict):
+    def _compute_new_headers(self, request_headers: HTTPHeadersDict) -> HTTPHeadersDict:
-        """
+        new_headers = HTTPHeadersDict()
-        Update the session headers with the request ones while ignoring
-        certain name prefixes.
-
-        """
-        headers = self.headers
         for name, value in request_headers.copy().items():
             if value is None:
                 continue  # Ignore explicitly unset headers
@@ -183,24 +212,40 @@ class Session(BaseConfigDict):
                         morsel['path'] = DEFAULT_COOKIE_PATH
                     self.cookie_jar.set(cookie_name, morsel)
 
-                all_cookie_headers = request_headers.getall(name)
+                request_headers.remove_item(name, original_value)
-                if len(all_cookie_headers) > 1:
-                    all_cookie_headers.remove(original_value)
-                else:
-                    request_headers.popall(name)
                 continue
 
             for prefix in SESSION_IGNORED_HEADER_PREFIXES:
                 if name.lower().startswith(prefix.lower()):
                     break
             else:
-                headers[name] = value
+                new_headers.add(name, value)
 
-        self['headers'] = dict(headers)
+        return new_headers
+
+    def update_headers(self, request_headers: HTTPHeadersDict):
+        """
+        Update the session headers with the request ones while ignoring
+        certain name prefixes.
+
+        """
+
+        new_headers = self._compute_new_headers(request_headers)
+        new_keys = new_headers.copy().keys()
+
+        # New headers will take priority over the existing ones, and override
+        # them directly instead of extending them.
+        for key, value in self._headers.copy().items():
+            if key in new_keys:
+                continue
+
+            new_headers.add(key, value)
+
+        self._headers = new_headers
 
     @property
     def headers(self) -> HTTPHeadersDict:
-        return HTTPHeadersDict(self['headers'])
+        return self._headers.copy()
 
     @property
     def cookies(self) -> RequestsCookieJar:
@@ -257,3 +302,17 @@ class Session(BaseConfigDict):
     @property
     def is_anonymous(self):
         return is_anonymous_session(self.session_id)
+
+    def warn_legacy_usage(self, warning: str) -> None:
+        if self.suppress_legacy_warnings:
+            return None
+
+        self.env.log_error(
+            warning,
+            level=Levels.WARNING
+        )
+
+        # We don't want to spam multiple warnings on each usage,
+        # so if there is already a warning for the legacy usage
+        # we'll skip the next ones.
+        self.suppress_legacy_warnings = True

tests/fixtures/session_data/new/cookies_dict.json

@@ -27,5 +27,5 @@
             "value": "bar"
         }
     ],
-    "headers": {}
+    "headers": []
 }

tests/fixtures/session_data/new/cookies_dict_dev_version.json

@@ -27,5 +27,5 @@
             "value": "bar"
         }
     ],
-    "headers": {}
+    "headers": []
 }

tests/fixtures/session_data/new/cookies_dict_with_extras.json

@@ -26,8 +26,14 @@
             "value": "bar"
         }
     ],
-    "headers": {
+    "headers": [
-        "X-Data": "value",
+        {
-        "X-Foo": "bar"
+            "name": "X-Data",
-    }
+            "value": "value"
+        },
+        {
+            "name": "X-Foo",
+            "value": "bar"
+        }
+    ]
 }

tests/fixtures/session_data/new/empty_cookies_dict.json

@@ -10,5 +10,5 @@
         "username": null
     },
     "cookies": [],
-    "headers": {}
+    "headers": []
 }

tests/fixtures/session_data/new/empty_cookies_list.json

@@ -10,5 +10,5 @@
         "username": null
     },
     "cookies": [],
-    "headers": {}
+    "headers": []
 }

tests/fixtures/session_data/new/empty_headers_dict.json

@@ -0,0 +1,14 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "__version__"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [],
+    "headers": []
+}

tests/fixtures/session_data/new/empty_headers_list.json

@@ -0,0 +1,14 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "__version__"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [],
+    "headers": []
+}

tests/fixtures/session_data/new/headers_cookies_dict_mixed.json

@@ -0,0 +1,40 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "__version__"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [
+        {
+            "domain": __host__,
+            "expires": null,
+            "name": "baz",
+            "path": "/",
+            "secure": false,
+            "value": "quux"
+        },
+        {
+            "domain": __host__,
+            "expires": null,
+            "name": "foo",
+            "path": "/",
+            "secure": false,
+            "value": "bar"
+        }
+    ],
+    "headers": [
+        {
+            "name": "X-Data",
+            "value": "value"
+        },
+        {
+            "name": "X-Foo",
+            "value": "bar"
+        }
+    ]
+}

tests/fixtures/session_data/new/headers_dict.json

@@ -0,0 +1,23 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "__version__"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [],
+    "headers": [
+        {
+            "name": "foo",
+            "value": "bar"
+        },
+        {
+            "name": "baz",
+            "value": "quux"
+        }
+    ]
+}

tests/fixtures/session_data/new/headers_dict_extras.json

@@ -0,0 +1,39 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "__version__"
+    },
+    "auth": {
+        "raw_auth": "foo:bar",
+        "type": "basic"
+    },
+    "cookies": [
+        {
+            "domain": null,
+            "expires": null,
+            "name": "baz",
+            "path": "/",
+            "secure": false,
+            "value": "quux"
+        },
+        {
+            "domain": null,
+            "expires": null,
+            "name": "foo",
+            "path": "/",
+            "secure": false,
+            "value": "bar"
+        }
+    ],
+    "headers": [
+        {
+            "name": "X-Data",
+            "value": "value"
+        },
+        {
+            "name": "X-Foo",
+            "value": "bar"
+        }
+    ]
+}

tests/fixtures/session_data/new/headers_list.json

@@ -0,0 +1,23 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "3.2.0"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [],
+    "headers": [
+        {
+            "name": "X-Data",
+            "value": "value"
+        },
+        {
+            "name": "X-Foo",
+            "value": "bar"
+        }
+    ]
+}

tests/fixtures/session_data/old/cookies_dict.json

@@ -23,5 +23,5 @@
             "value": "bar"
         }
     },
-    "headers": {}
+    "headers": []
 }

tests/fixtures/session_data/old/cookies_dict_dev_version.json

@@ -23,5 +23,5 @@
             "value": "bar"
         }
     },
-    "headers": {}
+    "headers": []
 }

tests/fixtures/session_data/old/cookies_dict_with_extras.json

@@ -22,8 +22,14 @@
             "value": "bar"
         }
     },
-    "headers": {
+    "headers": [
-        "X-Data": "value",
+        {
-        "X-Foo": "bar"
+            "name": "X-Data",
-    }
+            "value": "value"
+        },
+        {
+            "name": "X-Foo",
+            "value": "bar"
+        }
+    ]
 }

tests/fixtures/session_data/old/empty_cookies_dict.json

@@ -10,5 +10,5 @@
         "username": null
     },
     "cookies": {},
-    "headers": {}
+    "headers": []
 }

tests/fixtures/session_data/old/empty_cookies_list.json

@@ -10,5 +10,5 @@
         "username": null
     },
     "cookies": [],
-    "headers": {}
+    "headers": []
 }

tests/fixtures/session_data/old/empty_headers_dict.json

@@ -0,0 +1,14 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "3.0.2"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [],
+    "headers": {}
+}

tests/fixtures/session_data/old/empty_headers_list.json

@@ -0,0 +1,14 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "3.0.2"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [],
+    "headers": []
+}

tests/fixtures/session_data/old/headers_cookies_dict_mixed.json

@@ -0,0 +1,30 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "3.0.2"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": {
+        "baz": {
+            "expires": null,
+            "path": "/",
+            "secure": false,
+            "value": "quux"
+        },
+        "foo": {
+            "expires": null,
+            "path": "/",
+            "secure": false,
+            "value": "bar"
+        }
+    },
+    "headers": {
+        "X-Data": "value",
+        "X-Foo": "bar"
+    }
+}

tests/fixtures/session_data/old/headers_dict.json

@@ -0,0 +1,17 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "3.1.0"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [],
+    "headers": {
+        "foo": "bar",
+        "baz": "quux"
+    }
+}

tests/fixtures/session_data/old/headers_dict_extras.json

@@ -0,0 +1,33 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "3.1.0"
+    },
+    "auth": {
+        "raw_auth": "foo:bar",
+        "type": "basic"
+    },
+    "cookies": [
+        {
+            "domain": null,
+            "name": "baz",
+            "expires": null,
+            "path": "/",
+            "secure": false,
+            "value": "quux"
+        },
+        {
+            "domain": null,
+            "name": "foo",
+            "expires": null,
+            "path": "/",
+            "secure": false,
+            "value": "bar"
+        }
+    ],
+    "headers": {
+        "X-Data": "value",
+        "X-Foo": "bar"
+    }
+}

tests/fixtures/session_data/old/headers_list.json

@@ -0,0 +1,23 @@
+{
+    "__meta__": {
+        "about": "HTTPie session file",
+        "help": "https://httpie.io/docs#sessions",
+        "httpie": "3.2.0"
+    },
+    "auth": {
+        "password": null,
+        "type": null,
+        "username": null
+    },
+    "cookies": [],
+    "headers": [
+        {
+            "name": "X-Data",
+            "value": "value"
+        },
+        {
+            "name": "X-Foo",
+            "value": "bar"
+        }
+    ]
+}

tests/test_sessions.py

@@ -664,7 +664,7 @@ def test_old_session_cookie_layout_loading(basic_session, httpbin, mock_env):
 @pytest.mark.parametrize('layout_type', [
     dict, list
 ])
-def test_session_cookie_layout_preservance(basic_session, mock_env, layout_type):
+def test_session_cookie_layout_preservation(basic_session, mock_env, layout_type):
     with open_session(basic_session, mock_env) as session:
         session['cookies'] = layout_type()
         session.cookies.set('foo', 'bar')
@@ -677,7 +677,7 @@ def test_session_cookie_layout_preservance(basic_session, mock_env, layout_type)
 @pytest.mark.parametrize('layout_type', [
     dict, list
 ])
-def test_session_cookie_layout_preservance_on_new_cookies(basic_session, httpbin, mock_env, layout_type):
+def test_session_cookie_layout_preservation_on_new_cookies(basic_session, httpbin, mock_env, layout_type):
     with open_session(basic_session, mock_env) as session:
         session['cookies'] = layout_type()
         session.cookies.set('foo', 'bar')
@@ -690,3 +690,113 @@ def test_session_cookie_layout_preservance_on_new_cookies(basic_session, httpbin
 
     with open_session(basic_session, mock_env, read_only=True) as session:
         assert isinstance(session['cookies'], layout_type)
+
+
+@pytest.mark.parametrize('headers, expect_warning', [
+    # Old-style header format
+    (
+        {},
+        False
+    ),
+    (
+        {'Foo': 'bar'},
+        True
+    ),
+    # New style header format
+    (
+        [],
+        False
+    ),
+    (
+        [{'name': 'Foo', 'value': 'Bar'}],
+        False
+    ),
+])
+def test_headers_old_layout_warning(basic_session, mock_env, headers, expect_warning):
+    with open_raw_session(basic_session) as raw_session:
+        raw_session['headers'] = headers
+
+    with open_session(basic_session, mock_env, read_only=True):
+        warning = b'Outdated layout detected'
+        stderr = read_stderr(mock_env)
+
+        if expect_warning:
+            assert warning in stderr
+        else:
+            assert warning not in stderr
+
+
+def test_outdated_layout_mixed(basic_session, mock_env):
+    with open_raw_session(basic_session) as raw_session:
+        raw_session['headers'] = {'Foo': 'Bar'}
+        raw_session['cookies'] = {
+            'cookie': {
+                'value': 'value'
+            }
+        }
+
+    with open_session(basic_session, mock_env, read_only=True):
+        stderr = read_stderr(mock_env)
+        # We should only see 1 warning.
+        assert stderr.count(b'Outdated layout') == 1
+
+
+def test_old_session_header_layout_loading(basic_session, httpbin, mock_env):
+    with open_session(basic_session, mock_env) as session:
+        # Use the old layout & set a header
+        session['headers'] = {}
+        session._headers.add('Foo', 'Bar')
+
+    response = http(
+        '--session', str(basic_session),
+        httpbin + '/get'
+    )
+    assert response.json['headers']['Foo'] == 'Bar'
+
+
+@pytest.mark.parametrize('layout_type', [
+    dict, list
+])
+def test_session_header_layout_preservation(basic_session, mock_env, layout_type):
+    with open_session(basic_session, mock_env) as session:
+        session['headers'] = layout_type()
+        session._headers.add('Foo', 'Bar')
+
+    with open_session(basic_session, mock_env, read_only=True) as session:
+        assert isinstance(session['headers'], layout_type)
+
+
+@pytest.mark.parametrize('layout_type', [
+    dict, list
+])
+def test_session_header_layout_preservation_on_new_headers(basic_session, httpbin, mock_env, layout_type):
+    with open_session(basic_session, mock_env) as session:
+        session['headers'] = layout_type()
+        session._headers.add('Foo', 'Bar')
+
+    http(
+        '--session', str(basic_session),
+        httpbin + '/get',
+        'Baz:Quux'
+    )
+
+    with open_session(basic_session, mock_env, read_only=True) as session:
+        assert isinstance(session['headers'], layout_type)
+
+
+def test_session_multiple_headers_with_same_name(basic_session, httpbin):
+    http(
+        '--session', str(basic_session),
+        httpbin + '/get',
+        'Foo:bar',
+        'Foo:baz',
+        'Foo:bar'
+    )
+
+    r = http(
+        '--offline',
+        '--session', str(basic_session),
+        httpbin + '/get',
+    )
+    assert r.count('Foo: bar') == 2
+    assert 'Foo: baz' in r