diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index a169cf8ad..7417db81e 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -51,6 +51,10 @@ uv run pytest tests/unit -n auto
 uv run pytest tests/integration/codemod/test_codemods.py -n auto
 ```
 
+> [!TIP]
+>
+> - If on Linux the error `OSError: [Errno 24] Too many open files` appears then you might want to increase your _ulimit_
+
 ## Pull Request Process
 
 1. Fork the repository and create your branch from `develop`.
diff --git a/docs/building-with-codegen/imports.mdx b/docs/building-with-codegen/imports.mdx
index c66e7736d..95ecff990 100644
--- a/docs/building-with-codegen/imports.mdx
+++ b/docs/building-with-codegen/imports.mdx
@@ -69,6 +69,11 @@ print(f"From file: {import_stmt.from_file.filepath}")
 print(f"To file: {import_stmt.to_file.filepath}")
 ```
 
+<Note>
+With Python one can specify the `PYTHONPATH` environment variable which is then considered when resolving
+packages.
+</Note>
+
 ## Working with External Modules
 
 You can determine if an import references an [ExternalModule](/api-reference/core/ExternalModule) by checking the type of [Import.imported_symbol](/api-reference/core/Import#imported-symbol), like so:
diff --git a/src/codegen/cli/mcp/resources/system_prompt.py b/src/codegen/cli/mcp/resources/system_prompt.py
index a44bb2f38..9535570ab 100644
--- a/src/codegen/cli/mcp/resources/system_prompt.py
+++ b/src/codegen/cli/mcp/resources/system_prompt.py
@@ -2858,6 +2858,11 @@ def validate_data(data: dict) -> bool:
 print(f"To file: {import_stmt.to_file.filepath}")
 ```
 
+<Note>
+With Python one can specify the `PYTHONPATH` environment variable which is then considered when resolving
+packages.
+</Note>
+
 ## Working with External Modules
 
 You can determine if an import references an [ExternalModule](/api-reference/core/ExternalModule) by checking the type of [Import.imported_symbol](/api-reference/core/Import#imported-symbol), like so:
diff --git a/src/codegen/configs/models/codebase.py b/src/codegen/configs/models/codebase.py
index fcc7d3617..88643cfcd 100644
--- a/src/codegen/configs/models/codebase.py
+++ b/src/codegen/configs/models/codebase.py
@@ -17,7 +17,9 @@ def __init__(self, prefix: str = "CODEBASE", *args, **kwargs) -> None:
     disable_graph: bool = False
     disable_file_parse: bool = False
     generics: bool = True
+    import_resolution_paths: list[str] = Field(default_factory=lambda: [])
     import_resolution_overrides: dict[str, str] = Field(default_factory=lambda: {})
+    py_resolve_syspath: bool = False
     ts_dependency_manager: bool = False
     ts_language_engine: bool = False
     v8_ts_engine: bool = False
diff --git a/src/codegen/sdk/python/import_resolution.py b/src/codegen/sdk/python/import_resolution.py
index 46f9de63c..5cf8142ba 100644
--- a/src/codegen/sdk/python/import_resolution.py
+++ b/src/codegen/sdk/python/import_resolution.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import os
+import sys
 from typing import TYPE_CHECKING
 
 from codegen.sdk.core.autocommit import reader
@@ -104,6 +105,15 @@ def resolve_import(self, base_path: str | None = None, *, add_module_name: str |
                 base_path,
                 module_source.replace(".", "/") + "/" + symbol_name + ".py",
             )
+
+        # =====[ Check if we are importing an entire file with custom resolve path or sys.path enabled ]=====
+        if len(self.ctx.config.import_resolution_paths) > 0 or self.ctx.config.py_resolve_syspath:
+            # Handle resolve overrides first if both is set
+            resolve_paths: list[str] = self.ctx.config.import_resolution_paths + (sys.path if self.ctx.config.py_resolve_syspath else [])
+            if file := self._file_by_custom_resolve_paths(resolve_paths, filepath):
+                return ImportResolution(from_file=file, symbol=None, imports_file=True)
+
+        # =====[ Default path ]=====
         if file := self.ctx.get_file(filepath):
             return ImportResolution(from_file=file, symbol=None, imports_file=True)
 
@@ -113,8 +123,16 @@ def resolve_import(self, base_path: str | None = None, *, add_module_name: str |
             # You can't do `from a.b.c import foo` => `foo.utils.x` right now since `foo` is just a file...
             return ImportResolution(from_file=file, symbol=None, imports_file=True)
 
-        # =====[ Check if `module.py` file exists in the graph ]=====
+        # =====[ Check if `module.py` file exists in the graph with custom resolve path or sys.path enabled  ]=====
         filepath = module_source.replace(".", "/") + ".py"
+        if len(self.ctx.config.import_resolution_paths) > 0 or self.ctx.config.py_resolve_syspath:
+            # Handle resolve overrides first if both is set
+            resolve_paths: list[str] = self.ctx.config.import_resolution_paths + (sys.path if self.ctx.config.py_resolve_syspath else [])
+            if file := self._file_by_custom_resolve_paths(resolve_paths, filepath):
+                symbol = file.get_node_by_name(symbol_name)
+                return ImportResolution(from_file=file, symbol=symbol)
+
+        # =====[ Check if `module.py` file exists in the graph ]=====
         filepath = os.path.join(base_path, filepath)
         if file := self.ctx.get_file(filepath):
             symbol = file.get_node_by_name(symbol_name)
@@ -163,6 +181,20 @@ def resolve_import(self, base_path: str | None = None, *, add_module_name: str |
         # ext = ExternalModule.from_import(self)
         # return ImportResolution(symbol=ext)
 
+    @noapidoc
+    @reader
+    def _file_by_custom_resolve_paths(self, resolve_paths: list[str], filepath: str) -> SourceFile | None:
+        """Check if a certain file import can be found within a set sys.path
+        
+        Returns either None or the SourceFile.
+        """
+        for resolve_path in resolve_paths:
+            filepath_new: str = os.path.join(resolve_path, filepath)
+            if file := self.ctx.get_file(filepath_new):
+                return file
+
+        return None
+
     @noapidoc
     @reader
     def _relative_to_absolute_import(self, relative_import: str) -> str:
diff --git a/src/codegen/sdk/system-prompt.txt b/src/codegen/sdk/system-prompt.txt
index 1e6d6a904..95905981d 100644
--- a/src/codegen/sdk/system-prompt.txt
+++ b/src/codegen/sdk/system-prompt.txt
@@ -2879,6 +2879,11 @@ print(f"From file: {import_stmt.from_file.filepath}")
 print(f"To file: {import_stmt.to_file.filepath}")
 ```
 
+<Note>
+With Python one can specify the `PYTHONPATH` environment variable which is then considered when resolving
+packages.
+</Note>
+
 ## Working with External Modules
 
 You can determine if an import references an [ExternalModule](/api-reference/core/ExternalModule) by checking the type of [Import.imported_symbol](/api-reference/core/Import#imported-symbol), like so:
diff --git a/tests/unit/codegen/sdk/python/import_resolution/test_import_resolution.py b/tests/unit/codegen/sdk/python/import_resolution/test_import_resolution.py
index 63c58b5af..1fec2854a 100644
--- a/tests/unit/codegen/sdk/python/import_resolution/test_import_resolution.py
+++ b/tests/unit/codegen/sdk/python/import_resolution/test_import_resolution.py
@@ -1,3 +1,4 @@
+import sys
 from typing import TYPE_CHECKING
 
 from codegen.sdk.codebase.factory.get_session import get_codebase_session
@@ -191,7 +192,7 @@ def update():
             "consumer.py": """
 from a.b.c import src as operations
 
-def func_1():
+def func():
     operations.update()
 """,
         },
@@ -215,6 +216,232 @@ def func_1():
         assert call_site.file == consumer_file
 
 
+def test_import_resolution_file_syspath_inactive(tmpdir: str, monkeypatch) -> None:
+    """Tests function.usages returns usages from file imports"""
+    # language=python
+    with get_codebase_session(
+        tmpdir,
+        files={
+            "a/b/c/src.py": """
+def update():
+    pass
+""",
+            "consumer.py": """
+from b.c import src as operations
+
+def func():
+    operations.update()
+""",
+        },
+    ) as codebase:
+        src_file: SourceFile = codebase.get_file("a/b/c/src.py")
+        consumer_file: SourceFile = codebase.get_file("consumer.py")
+
+        # Disable resolution via sys.path
+        codebase.ctx.config.py_resolve_syspath = False
+
+        # =====[ Imports cannot be found without sys.path being set and not active ]=====
+        assert len(consumer_file.imports) == 1
+        src_import: Import = consumer_file.imports[0]
+        src_import_resolution: ImportResolution = src_import.resolve_import()
+        assert src_import_resolution is None
+
+        # Modify sys.path for this test only
+        monkeypatch.syspath_prepend("a")
+
+        # =====[ Imports cannot be found with sys.path set but not active ]=====
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution is None
+
+
+def test_import_resolution_file_syspath_active(tmpdir: str, monkeypatch) -> None:
+    """Tests function.usages returns usages from file imports"""
+    # language=python
+    with get_codebase_session(
+        tmpdir,
+        files={
+            "a/b/c/src.py": """
+def update():
+    pass
+""",
+            "consumer.py": """
+from b.c import src as operations
+
+def func():
+    operations.update()
+""",
+        },
+    ) as codebase:
+        src_file: SourceFile = codebase.get_file("a/b/c/src.py")
+        consumer_file: SourceFile = codebase.get_file("consumer.py")
+
+        # Enable resolution via sys.path
+        codebase.ctx.config.py_resolve_syspath = True
+
+        # =====[ Imports cannot be found without sys.path being set ]=====
+        assert len(consumer_file.imports) == 1
+        src_import: Import = consumer_file.imports[0]
+        src_import_resolution: ImportResolution = src_import.resolve_import()
+        assert src_import_resolution is None
+
+        # Modify sys.path for this test only
+        monkeypatch.syspath_prepend("a")
+
+        # =====[ Imports can be found with sys.path set and active ]=====
+        codebase.ctx.config.py_resolve_syspath = True
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution 
+        assert src_import_resolution.from_file is src_file
+        assert src_import_resolution.imports_file is True
+
+
+def test_import_resolution_file_custom_resolve_path(tmpdir: str) -> None:
+    """Tests function.usages returns usages from file imports"""
+    # language=python
+    with get_codebase_session(
+        tmpdir,
+        files={
+            "a/b/c/src.py": """
+def update():
+    pass
+""",
+            "consumer.py": """
+from b.c import src as operations
+from c import src as operations2
+
+def func():
+    operations.update()
+""",
+        },
+    ) as codebase:
+        src_file: SourceFile = codebase.get_file("a/b/c/src.py")
+        consumer_file: SourceFile = codebase.get_file("consumer.py")
+
+        # =====[ Imports cannot be found without custom resolve path being set ]=====
+        assert len(consumer_file.imports) == 2
+        src_import: Import = consumer_file.imports[0]
+        src_import_resolution: ImportResolution = src_import.resolve_import()
+        assert src_import_resolution is None
+
+        # =====[ Imports cannot be found with custom resolve path set to invalid path ]=====
+        codebase.ctx.config.import_resolution_paths = ["x"]
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution is None
+
+        # =====[ Imports can be found with custom resolve path set ]=====
+        codebase.ctx.config.import_resolution_paths = ["a"]
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution 
+        assert src_import_resolution.from_file is src_file
+        assert src_import_resolution.imports_file is True
+
+        # =====[ Imports can be found with custom resolve multi-path set ]=====
+        src_import = consumer_file.imports[1]
+        codebase.ctx.config.import_resolution_paths = ["a/b"]
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution 
+        assert src_import_resolution.from_file is src_file
+        assert src_import_resolution.imports_file is True
+
+
+def test_import_resolution_file_custom_resolve_and_syspath_precedence(tmpdir: str, monkeypatch) -> None:
+    """Tests function.usages returns usages from file imports"""
+    # language=python
+    with get_codebase_session(
+        tmpdir,
+        files={
+            "a/c/src.py": """
+def update1():
+    pass
+""",
+            "a/b/c/src.py": """
+def update2():
+    pass
+""",
+            "consumer.py": """
+from c import src as operations
+
+def func():
+    operations.update2()
+""",
+        },
+    ) as codebase:
+        src_file: SourceFile = codebase.get_file("a/b/c/src.py")
+        consumer_file: SourceFile = codebase.get_file("consumer.py")
+
+        # Ensure we don't have overrites and enable syspath resolution
+        codebase.ctx.config.import_resolution_paths = []
+        codebase.ctx.config.py_resolve_syspath = True
+
+        # =====[ Import with sys.path set can be found ]=====
+        assert len(consumer_file.imports) == 1
+        # Modify sys.path for this test only
+        monkeypatch.syspath_prepend("a")
+        src_import: Import = consumer_file.imports[0]
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution 
+        assert src_import_resolution.from_file.file_path == "a/c/src.py"
+
+        # =====[ Imports can be found with custom resolve over sys.path ]=====
+        codebase.ctx.config.import_resolution_paths = ["a/b"]
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution 
+        assert src_import_resolution.from_file is src_file
+        assert src_import_resolution.imports_file is True
+
+
+def test_import_resolution_default_conflicts_overrite(tmpdir: str, monkeypatch) -> None:
+    """Tests function.usages returns usages from file imports"""
+    # language=python
+    with get_codebase_session(
+        tmpdir,
+        files={
+            "a/src.py": """
+def update1():
+    pass
+""",
+            "b/a/src.py": """
+def update2():
+    pass
+""",
+            "consumer.py": """
+from a import src as operations
+
+def func():
+    operations.update2()
+""",
+        },
+    ) as codebase:
+        src_file: SourceFile = codebase.get_file("a/src.py")
+        src_file_overrite: SourceFile = codebase.get_file("b/a/src.py")
+        consumer_file: SourceFile = codebase.get_file("consumer.py")
+
+        # Ensure we don't have overrites and enable syspath resolution
+        codebase.ctx.config.import_resolution_paths = []
+        codebase.ctx.config.py_resolve_syspath = True
+
+        # =====[ Default import works ]=====
+        assert len(consumer_file.imports) == 1
+        src_import: Import = consumer_file.imports[0]
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution 
+        assert src_import_resolution.from_file is src_file
+
+        # =====[ Sys.path overrite has precedence ]=====
+        monkeypatch.syspath_prepend("b")
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution 
+        assert src_import_resolution.from_file is not src_file
+        assert src_import_resolution.from_file is src_file_overrite
+
+        # =====[ Custom overrite has precedence ]=====
+        codebase.ctx.config.import_resolution_paths = ["b"]
+        src_import_resolution = src_import.resolve_import()
+        assert src_import_resolution 
+        assert src_import_resolution.from_file is not src_file
+        assert src_import_resolution.from_file is src_file_overrite
+
+
 def test_import_resolution_init_wildcard(tmpdir: str) -> None:
     """Tests that named import from a file with wildcard resolves properly"""
     # language=python