diff --git a/aea/configurations/base.py b/aea/configurations/base.py
index a685f01262..39c56a1ec6 100644
--- a/aea/configurations/base.py
+++ b/aea/configurations/base.py
@@ -94,7 +94,12 @@
 T = TypeVar("T")
 
 
-def dependencies_from_json(obj: Dict[str, Dict]) -> Dependencies:
+def as_posix_str(path: Union[Path, str]) -> str:
+    """Cast to POSIX format"""
+    return str(Path(path).as_posix())
+
+
+def dependencies_from_json(obj: Dict[str, Dict[str, str]]) -> Dependencies:
     """
     Parse a JSON object to get an instance of Dependencies.
 
@@ -104,7 +109,7 @@ def dependencies_from_json(obj: Dict[str, Dict]) -> Dependencies:
     return {key: Dependency.from_json({key: value}) for key, value in obj.items()}
 
 
-def dependencies_to_json(dependencies: Dependencies) -> Dict[str, Dict]:
+def dependencies_to_json(dependencies: Dependencies) -> Dict[str, Dict[str, str]]:
     """
     Transform a Dependencies object into a JSON object.
 
@@ -113,13 +118,14 @@ def dependencies_to_json(dependencies: Dependencies) -> Dict[str, Dict]:
              values are the JSON version of a Dependency object.
     """
     result = {}
-    for key, value in dependencies.items():
-        dep_to_json = value.to_json()
-        package_name = list(dep_to_json.items())[0][0]
+    for key, dependency in dependencies.items():
+        dep_to_json = dependency.to_json()
+        enforce(len(dep_to_json) == 1, f"Expecting single item, found: {dep_to_json}")
+        package_name, package_json = dep_to_json.popitem()
         enforce(
             key == package_name, f"Names of dependency differ: {key} != {package_name}"
         )
-        result[key] = dep_to_json[key]
+        result[key] = package_json
     return result
 
 
@@ -716,9 +722,9 @@ def json(self) -> Dict:
         if self.cert_requests is not None:
             result["cert_requests"] = list(map(attrgetter("json"), self.cert_requests))
         if self.build_entrypoint:
-            result["build_entrypoint"] = self.build_entrypoint
+            result["build_entrypoint"] = as_posix_str(self.build_entrypoint)
         if self.build_directory:
-            result["build_directory"] = self.build_directory
+            result["build_directory"] = as_posix_str(self.build_directory)
         return result
 
     @classmethod
@@ -848,9 +854,9 @@ def json(self) -> Dict:
             }
         )
         if self.build_entrypoint:
-            result["build_entrypoint"] = self.build_entrypoint
+            result["build_entrypoint"] = as_posix_str(self.build_entrypoint)
         if self.build_directory:
-            result["build_directory"] = self.build_directory
+            result["build_directory"] = as_posix_str(self.build_directory)
         return result
 
     @classmethod
@@ -905,7 +911,7 @@ def json(self) -> Dict:
         """Return the JSON representation."""
         result = {"class_name": self.class_name, "args": self.args}
         if self.file_path is not None:
-            result["file_path"] = str(self.file_path.as_posix())
+            result["file_path"] = as_posix_str(self.file_path)
         return result
 
     @classmethod
@@ -1066,9 +1072,9 @@ def json(self) -> Dict:
             }
         )
         if self.build_entrypoint:
-            result["build_entrypoint"] = self.build_entrypoint
+            result["build_entrypoint"] = as_posix_str(self.build_entrypoint)
         if self.build_directory:
-            result["build_directory"] = self.build_directory
+            result["build_directory"] = as_posix_str(self.build_directory)
         return result
 
     @classmethod
@@ -1373,14 +1379,15 @@ def package_dependencies(self) -> Set[ComponentId]:
     def private_key_paths_dict(self) -> Dict[str, str]:
         """Get dictionary version of private key paths."""
         return {  # pylint: disable=unnecessary-comprehension
-            key: path for key, path in self.private_key_paths.read_all()
+            key: as_posix_str(path) for key, path in self.private_key_paths.read_all()
         }
 
     @property
     def connection_private_key_paths_dict(self) -> Dict[str, str]:
         """Get dictionary version of connection private key paths."""
         return {  # pylint: disable=unnecessary-comprehension
-            key: path for key, path in self.connection_private_key_paths.read_all()
+            key: as_posix_str(path)
+            for key, path in self.connection_private_key_paths.read_all()
         }
 
     def component_configurations_json(self) -> List[OrderedDict]:
@@ -1430,7 +1437,7 @@ def json(self) -> Dict:
         )  # type: Dict[str, Any]
 
         if self.build_entrypoint:
-            config["build_entrypoint"] = self.build_entrypoint
+            config["build_entrypoint"] = as_posix_str(self.build_entrypoint)
 
         # framework optional configs are only printed if defined.
         if self.period is not None:
@@ -1814,15 +1821,18 @@ def json(self) -> Dict:
                 "fingerprint": self.fingerprint,
                 "fingerprint_ignore_patterns": self.fingerprint_ignore_patterns,
                 "class_name": self.class_name,
-                "contract_interface_paths": self.contract_interface_paths,
+                "contract_interface_paths": {
+                    key: as_posix_str(path)
+                    for key, path in self.contract_interface_paths.items()
+                },
                 "dependencies": dependencies_to_json(self.dependencies),
                 CONTRACTS: sorted(map(str, self.contracts)),
             }
         )
         if self.build_entrypoint:
-            result["build_entrypoint"] = self.build_entrypoint
+            result["build_entrypoint"] = as_posix_str(self.build_entrypoint)
         if self.build_directory:
-            result["build_directory"] = self.build_directory
+            result["build_directory"] = as_posix_str(self.build_directory)
         return result
 
     @classmethod
diff --git a/docs/api/configurations/base.md b/docs/api/configurations/base.md
index 24b0890d92..9091e4028a 100644
--- a/docs/api/configurations/base.md
+++ b/docs/api/configurations/base.md
@@ -4,12 +4,22 @@
 
 Classes to handle AEA configurations.
 
+<a id="aea.configurations.base.as_posix_str"></a>
+
+#### as`_`posix`_`str
+
+```python
+def as_posix_str(path: Union[Path, str]) -> str
+```
+
+Cast to POSIX format
+
 <a id="aea.configurations.base.dependencies_from_json"></a>
 
 #### dependencies`_`from`_`json
 
 ```python
-def dependencies_from_json(obj: Dict[str, Dict]) -> Dependencies
+def dependencies_from_json(obj: Dict[str, Dict[str, str]]) -> Dependencies
 ```
 
 Parse a JSON object to get an instance of Dependencies.
@@ -27,7 +37,7 @@ a Dependencies object.
 #### dependencies`_`to`_`json
 
 ```python
-def dependencies_to_json(dependencies: Dependencies) -> Dict[str, Dict]
+def dependencies_to_json(dependencies: Dependencies) -> Dict[str, Dict[str, str]]
 ```
 
 Transform a Dependencies object into a JSON object.
diff --git a/tests/test_configurations/test_base.py b/tests/test_configurations/test_base.py
index 818491bd49..ef0f888187 100644
--- a/tests/test_configurations/test_base.py
+++ b/tests/test_configurations/test_base.py
@@ -18,9 +18,14 @@
 #
 # ------------------------------------------------------------------------------
 """This module contains the tests for the aea.configurations.base module."""
+import hashlib
+import json
 import re
+import string
+import tempfile
 from copy import copy
 from pathlib import Path
+from typing import Iterable, List, Union
 from unittest import TestCase, mock
 from unittest.mock import Mock
 
@@ -43,11 +48,13 @@
     ProtocolConfig,
     ProtocolSpecification,
     PublicId,
+    SkillComponentConfiguration,
     SkillConfig,
     SpeechActContentConfig,
     _check_aea_version,
     _compare_fingerprints,
     _get_default_configuration_file_name_from_type,
+    as_posix_str,
     dependencies_from_json,
     dependencies_to_json,
 )
@@ -59,6 +66,7 @@
     DEFAULT_SKILL_CONFIG_FILE,
 )
 from aea.configurations.loader import ConfigLoaders, load_component_configuration
+from aea.helpers.yaml_utils import yaml_dump, yaml_load
 
 from tests.conftest import (
     AUTHOR,
@@ -1123,3 +1131,138 @@ def test_component_id_from_json():
         "version": "1.0.0",
     }
     assert ComponentId.from_json(json_data).json == json_data
+
+
+class TestConfigurationContainingPathSerialization:
+    """Test configurations containing paths are deterministic across different OS"""
+
+    def setup(self):
+        """Setup test"""
+
+        # starting from posix-compliant format
+        self.raw_paths = [
+            "C:/Documents/Newsletters/Summer2018.pdf",
+            "/Program Files/Custom Utilities/StringFinder.exe",
+            "2018/January.xlsx",
+            "../Publications/TravelBrochure.pdf",
+            "C:/Projects/apilibrary/apilibrary.sln",
+            "C:Projects/apilibrary/apilibrary.sln",
+            "c:/temp/test-file.txt",
+            "//127.0.0.1/c$/temp/test-file.txt",
+            "//LOCALHOST/c$/temp/test-file.txt",
+            "//c:/temp/test-file.txt",
+            "//?/c:/temp/test-file.txt",
+            "//UNC/LOCALHOST/c$/temp/test-file.txt",
+            "jquery-1.1.1.js",
+            "jquery-1.1.1.min.js",
+            "jquery-1.1.1-vsdoc.js",
+            "jquery-1.2.1-vsdoc.js",
+            "jquery-1.2.1.js",
+            "jquery-1.2.1.min.js",
+        ]
+
+    def yaml_config_dump_load_equal(self, data: dict) -> bool:
+        """Check whether config is the same after yaml dump and load"""
+
+        with tempfile.TemporaryDirectory() as tmp_dir:
+            tmp_file = Path(tmp_dir) / "tmp_file"
+            with open(tmp_file, "w") as stream:
+                yaml_dump(data, stream)
+            with open(tmp_file, "r") as stream:
+                reconstituted_data = yaml_load(stream)
+            return data == reconstituted_data
+
+    def same_after_casting_to_posix_string(self, config) -> bool:
+        """Check serialization same after casting string values to POSIX"""
+
+        def is_iterable_non_string(obj) -> bool:
+            return not isinstance(obj, str) and isinstance(obj, Iterable)
+
+        def to_posix(obj):
+            if is_iterable_non_string(obj):
+                if isinstance(obj, dict):
+                    return {k: to_posix(v) for k, v in obj.items()}
+                return obj.__class__(*map(to_posix, obj))
+            # empty string to posix == "." hence we do not cast it.
+            return as_posix_str(obj) if obj and isinstance(obj, str) else obj
+
+        return to_posix(config.json) == config.json
+
+    def get_hexdigest_from_config_json(
+        self,
+        config: Union[
+            SkillComponentConfiguration, SkillConfig, AgentConfig, ContractConfig
+        ],
+    ) -> str:
+        """Get hexdigest from the json serialized configuration"""
+
+        # this is tested because we assume config.json is deterministic
+        return hashlib.sha512(json.dumps(config.json).encode("utf-8")).hexdigest()
+
+    def test_filepath_ordering(self) -> None:
+        """Test that filepath ordering remains equivalent when converting to POSIX"""
+
+        # https://learn.microsoft.com/en-us/dotnet/standard/io/file-path-formats
+
+        def sorted_indices(li: List[str]) -> List[int]:
+            return sorted(range(len(li)), key=lambda i: li[i])
+
+        # since automagically converted to POSIX compliant-format when on Linux,
+        # hard-coded the expected posix order to ensure consistency across OS.
+        posix_paths = [Path(p).as_posix() for p in self.raw_paths]
+        expected = [3, 7, 10, 8, 11, 9, 1, 2, 0, 4, 5, 6, 14, 12, 13, 15, 16, 17]
+        assert sorted_indices(self.raw_paths) == sorted_indices(posix_paths)
+        assert sorted_indices(self.raw_paths) == expected
+
+    def test_skill_component_configuration_serialization(self) -> None:
+        """Test SkillComponentConfiguration serialization"""
+
+        config = SkillComponentConfiguration(
+            class_name="class_name", file_path=self.raw_paths[0]
+        )
+        assert self.yaml_config_dump_load_equal(config.json)
+        assert self.same_after_casting_to_posix_string(config)
+
+    def test_skill_configuration_serialization(self) -> None:
+        """Test SkillConfig serialization"""
+
+        name, author = "name", "author"
+        config = SkillConfig(
+            name=name,
+            author=author,
+            build_entrypoint=self.raw_paths[0],
+            build_directory=self.raw_paths[0],
+        )
+        assert self.yaml_config_dump_load_equal(config.json)
+        assert self.same_after_casting_to_posix_string(config)
+
+    def test_agent_configuration_serialization(self) -> None:
+        """Test AgentConfig serialization"""
+
+        agent_name, author = "agent_name", "author"
+        config = AgentConfig(
+            agent_name=agent_name,
+            author=author,
+            build_entrypoint=self.raw_paths[0],
+            data_dir=self.raw_paths[0],
+        )
+        for dummy_key, raw_path in zip(string.ascii_letters, self.raw_paths):
+            config.private_key_paths.create(dummy_key, raw_path)
+            config.connection_private_key_paths.create(dummy_key, raw_path)
+        assert self.yaml_config_dump_load_equal(config.json)
+        assert self.same_after_casting_to_posix_string(config)
+
+    def test_contract_configuration_serialization(self) -> None:
+        """Test ContractConfig serialization"""
+
+        name, author = "name", "author"
+        path_dict = dict(zip(string.ascii_letters, self.raw_paths))
+        config = ContractConfig(
+            name=name,
+            author=author,
+            build_entrypoint=self.raw_paths[0],
+            build_directory=self.raw_paths[0],
+            contract_interface_paths=path_dict,
+        )
+        assert self.yaml_config_dump_load_equal(config.json)
+        assert self.same_after_casting_to_posix_string(config)