diff --git a/pyproject.toml b/pyproject.toml
index c8806c1..8b4d4db 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -125,7 +125,7 @@ addopts = [
     "--cov-report=xml:build/coverage/coverage.xml",
     "--cov-report=term-missing",
     "--numprocesses=auto",
-    "--timeout=30"
+    "--timeout=60"
 ]
 
 
@@ -141,4 +141,4 @@ source = [
 
 [tool.coverage.report]
 show_missing = true
-fail_under = 92
\ No newline at end of file
+fail_under = 92
diff --git a/src/openjd/cli/_common/__init__.py b/src/openjd/cli/_common/__init__.py
index ee26ea1..d970dee 100644
--- a/src/openjd/cli/_common/__init__.py
+++ b/src/openjd/cli/_common/__init__.py
@@ -7,6 +7,7 @@
 from typing import Callable, Literal
 import json
 import yaml
+import os
 
 from ._job_from_template import (
     job_from_template,
@@ -100,14 +101,15 @@ def add(self, name: str, description: str, **kwargs) -> ArgumentParser:
 def generate_job(args: Namespace) -> Job:
     try:
         # Raises: RuntimeError, DecodeValidationError
-        _, template = read_template(args)
+        template_file, template = read_template(args)
         # Raises: RuntimeError
-        sample_job = job_from_template(template, args.job_params if args.job_params else None)
+        return job_from_template(
+            template, args.job_params if args.job_params else None, Path(os.path.abspath(template_file.parent)), Path(os.getcwd())
+        )
     except RuntimeError as rte:
         raise RuntimeError(f"ERROR generating Job: {str(rte)}")
     except DecodeValidationError as dve:
         raise RuntimeError(f"ERROR validating template: {str(dve)}")
-    return sample_job
 
 
 @dataclass
diff --git a/src/openjd/cli/_common/_job_from_template.py b/src/openjd/cli/_common/_job_from_template.py
index 86f7470..c0f3317 100644
--- a/src/openjd/cli/_common/_job_from_template.py
+++ b/src/openjd/cli/_common/_job_from_template.py
@@ -159,7 +159,12 @@ def get_task_params(arguments: list[list[str]]) -> list[dict[str, str]]:
     return all_parameter_sets
 
 
-def job_from_template(template: JobTemplate, parameter_args: list[str] | None = None) -> Job:
+def job_from_template(
+    template: JobTemplate,
+    parameter_args: list[str] | None,
+    job_template_dir: Path,
+    current_working_dir: Path,
+) -> Job:
     """
     Given a decoded Job Template and a user-inputted parameter dictionary,
     generates a Job object.
@@ -170,7 +175,10 @@ def job_from_template(template: JobTemplate, parameter_args: list[str] | None =
 
     try:
         parameter_values = preprocess_job_parameters(
-            job_template=template, job_parameter_values=parameter_dict
+            job_template=template,
+            job_parameter_values=parameter_dict,
+            job_template_dir=job_template_dir,
+            current_working_dir=current_working_dir,
         )
     except ValueError as ve:
         raise RuntimeError(f"Parameters can't be used with Template: {str(ve)}")
diff --git a/test/openjd/cli/conftest.py b/test/openjd/cli/conftest.py
index 6227260..0bfcd9f 100644
--- a/test/openjd/cli/conftest.py
+++ b/test/openjd/cli/conftest.py
@@ -1,6 +1,9 @@
 # Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
 
+import os
 import pytest
+import tempfile
+from pathlib import Path
 from unittest.mock import patch
 
 from . import MOCK_TEMPLATE, SampleSteps
@@ -10,18 +13,36 @@
 
 
 @pytest.fixture(scope="function", params=[[], ["Message='A new message!'"]])
-def sample_job(request):
+def sample_job_and_dirs(request):
     """
     Uses the MOCK_TEMPLATE object to create a Job, once
     with default parameters and once with user-specified parameters.
+
+    This fixture also manages the life time of a temporary directory that's
+    used for the job template dir and the current working directory.
     """
-    template = decode_template(template=MOCK_TEMPLATE)
-    return job_from_template(template=template, parameter_args=request.param)
+    with tempfile.TemporaryDirectory() as tmpdir:
+        template_dir = Path(tmpdir) / "template_dir"
+        current_working_dir = Path(tmpdir) / "current_working_dir"
+        os.makedirs(template_dir)
+        os.makedirs(current_working_dir)
+
+        template = decode_template(template=MOCK_TEMPLATE)
+        yield (
+            job_from_template(
+                template=template,
+                parameter_args=request.param,
+                job_template_dir=template_dir,
+                current_working_dir=current_working_dir,
+            ),
+            template_dir,
+            current_working_dir,
+        )
 
 
 @pytest.fixture(scope="function")
-def sample_step_map(sample_job):
-    return {step.name: step for step in sample_job.steps}
+def sample_step_map(sample_job_and_dirs):
+    return {step.name: step for step in sample_job_and_dirs[0].steps}
 
 
 @pytest.fixture(
diff --git a/test/openjd/cli/test_common.py b/test/openjd/cli/test_common.py
index f8dc9a3..48dca3d 100644
--- a/test/openjd/cli/test_common.py
+++ b/test/openjd/cli/test_common.py
@@ -28,6 +28,21 @@
 )
 
 
+@pytest.fixture(scope="function")
+def template_dir_and_cwd():
+    """
+    This fixture manages the life time of a temporary directory that's
+    used for the job template dir and the current working directory.
+    """
+    with tempfile.TemporaryDirectory() as tmpdir:
+        template_dir = Path(tmpdir) / "template_dir"
+        current_working_dir = Path(tmpdir) / "current_working_dir"
+        os.makedirs(template_dir)
+        os.makedirs(current_working_dir)
+
+        yield (template_dir, current_working_dir)
+
+
 @patch("openjd.cli._common._validation_utils.decode_template")
 def test_decode_template_called(mock_decode_template: Mock):
     """
@@ -335,13 +350,16 @@ def test_get_job_params_error(
         ),
     ],
 )
-def test_job_from_template_success(mock_params: list, expected_job_name: str, template_dict: dict):
+def test_job_from_template_success(
+    mock_params: list, expected_job_name: str, template_dict: dict, template_dir_and_cwd: tuple
+):
     """
     Test that `job_from_template` creates a Job with the provided parameters.
     """
+    template_dir, current_working_dir = template_dir_and_cwd
     template = decode_template(template=template_dict)
 
-    result = job_from_template(template, mock_params)
+    result = job_from_template(template, mock_params, template_dir, current_working_dir)
     assert result.name == expected_job_name
     assert result.steps == template.steps
     if result.parameters:
@@ -377,15 +395,18 @@ def test_job_from_template_success(mock_params: list, expected_job_name: str, te
         ),
     ],
 )
-def test_job_from_template_error(mock_params: list, template_dict: dict, expected_error: str):
+def test_job_from_template_error(
+    mock_params: list, template_dict: dict, expected_error: str, template_dir_and_cwd: tuple
+):
     """
     Test that errors thrown by `job_from_template` have expected information
     """
+    template_dir, current_working_dir = template_dir_and_cwd
 
     template = decode_template(template=template_dict)
 
     with pytest.raises(RuntimeError) as rte:
-        job_from_template(template, mock_params)
+        job_from_template(template, mock_params, template_dir, current_working_dir)
 
     assert expected_error in str(rte.value)
 
@@ -563,6 +584,8 @@ def test_generate_job_success(
         new=Mock(side_effect=job_from_template),
     ) as patched_job_from_template:
         generate_job(mock_args)
-        patched_job_from_template.assert_called_once_with(ANY, expected_param_list)
+        patched_job_from_template.assert_called_once_with(
+            ANY, expected_param_list, Path(temp_template.name).parent, Path(os.getcwd())
+        )
 
     Path(temp_template.name).unlink()
diff --git a/test/openjd/cli/test_local_session.py b/test/openjd/cli/test_local_session.py
index 4d010c8..e322b00 100644
--- a/test/openjd/cli/test_local_session.py
+++ b/test/openjd/cli/test_local_session.py
@@ -36,7 +36,7 @@ def patched_actions():
         yield patched_enter, patched_run, patched_exit, patched_callback
 
 
-@pytest.mark.usefixtures("sample_job")
+@pytest.mark.usefixtures("sample_job_and_dirs")
 @pytest.mark.parametrize(
     "given_parameters,expected_parameters",
     [
@@ -63,11 +63,12 @@ def patched_actions():
     ],
 )
 def test_generate_task_parameter_set(
-    sample_job: Job, given_parameters: dict, expected_parameters: dict
+    sample_job_and_dirs: tuple, given_parameters: dict, expected_parameters: dict
 ):
     """
     Test that a LocalSession can generate Task parameters given valid user input.
     """
+    sample_job, template_dir, current_working_dir = sample_job_and_dirs
     with LocalSession(job=sample_job, session_id="my-session") as session:
         # Convince the type checker that `parameterSpace` exists
         param_space = sample_job.steps[SampleSteps.TaskParamStep].parameterSpace
@@ -82,10 +83,10 @@ def test_generate_task_parameter_set(
             )
 
 
-@pytest.mark.usefixtures("sample_job")
+@pytest.mark.usefixtures("sample_job_and_dirs")
 @pytest.mark.parametrize(*SESSION_PARAMETERS)
 def test_localsession_initialize(
-    sample_job: Job,
+    sample_job_and_dirs: tuple,
     dependency_indexes: list[int],
     step_index: int,
     maximum_tasks: int,
@@ -97,6 +98,7 @@ def test_localsession_initialize(
     Test that initializing the local Session clears the `ended` flag, only generates Task parameters
     when necessary, and adds to the Action queue appropriately.
     """
+    sample_job, template_dir, current_working_dir = sample_job_and_dirs
     with LocalSession(job=sample_job, session_id="my-session") as session:
         with patch.object(
             LocalSession,
@@ -121,9 +123,10 @@ def test_localsession_initialize(
         assert session._action_queue.qsize() == 2 * num_expected_environments + num_expected_tasks
 
 
-@pytest.mark.usefixtures("sample_job")
-def test_localsession_traps_sigint(sample_job: Job):
+@pytest.mark.usefixtures("sample_job_and_dirs")
+def test_localsession_traps_sigint(sample_job_and_dirs: tuple):
     # Make sure that we hook up, and remove the signal handler when using the local session
+    sample_job, template_dir, current_working_dir = sample_job_and_dirs
 
     # GIVEN
     with patch.object(local_session_mod, "signal") as signal_mod:
@@ -143,10 +146,10 @@ def test_localsession_traps_sigint(sample_job: Job):
     )
 
 
-@pytest.mark.usefixtures("sample_job", "capsys")
+@pytest.mark.usefixtures("sample_job_and_dirs", "capsys")
 @pytest.mark.parametrize(*SESSION_PARAMETERS)
 def test_localsession_run_success(
-    sample_job: Job,
+    sample_job_and_dirs: tuple,
     capsys: pytest.CaptureFixture,
     dependency_indexes: list[int],
     step_index: int,
@@ -159,6 +162,7 @@ def test_localsession_run_success(
     Test that calling `run` causes the local Session to
     iterate through the actions defined in the Job.
     """
+    sample_job, template_dir, current_working_dir = sample_job_and_dirs
     with LocalSession(job=sample_job, session_id="my-session") as session:
         session.initialize(
             dependencies=[sample_job.steps[i] for i in dependency_indexes],
@@ -182,11 +186,12 @@ def test_localsession_run_success(
     )
 
 
-@pytest.mark.usefixtures("sample_job")
-def test_localsession_run_not_ready(sample_job: Job):
+@pytest.mark.usefixtures("sample_job_and_dirs")
+def test_localsession_run_not_ready(sample_job_and_dirs: tuple):
     """
     Test that a LocalSession throws an error when it is not in the "READY" state.
     """
+    sample_job, template_dir, current_working_dir = sample_job_and_dirs
     with LocalSession(job=sample_job, session_id="my-session") as session:
         with patch.object(Session, "state", new=SessionState.ENDED), pytest.raises(
             RuntimeError
@@ -196,11 +201,12 @@ def test_localsession_run_not_ready(sample_job: Job):
     assert "not in a READY state" in str(rte.value)
 
 
-@pytest.mark.usefixtures("sample_job", "capsys")
-def test_localsession_run_failed(sample_job: Job, capsys: pytest.CaptureFixture):
+@pytest.mark.usefixtures("sample_job_and_dirs", "capsys")
+def test_localsession_run_failed(sample_job_and_dirs: tuple, capsys: pytest.CaptureFixture):
     """
     Test that a LocalSession can gracefully handle an error in its inner Session.
     """
+    sample_job, template_dir, current_working_dir = sample_job_and_dirs
     with LocalSession(job=sample_job, session_id="bad-session") as session:
         session.initialize(dependencies=[], step=sample_job.steps[SampleSteps.BadCommand])
         session.run()
diff --git a/test/openjd/cli/test_run_command.py b/test/openjd/cli/test_run_command.py
index 37af056..1da39b6 100644
--- a/test/openjd/cli/test_run_command.py
+++ b/test/openjd/cli/test_run_command.py
@@ -2,7 +2,7 @@
 
 from argparse import Namespace
 import json
-from pathlib import Path, PureWindowsPath, PurePosixPath
+from pathlib import Path, PurePath, PureWindowsPath, PurePosixPath
 import tempfile
 
 import pytest
@@ -107,7 +107,7 @@ def test_do_run_path_mapping_rules():
         PathMappingRule(
             source_path_format=PathFormat.WINDOWS,
             source_path=PureWindowsPath(r"C:\test"),
-            destination_path=PurePosixPath("/mnt/test"),
+            destination_path=PurePath("/mnt/test"),
         )
     ]
 
@@ -187,7 +187,7 @@ def test_do_run_nonexistent_step(capsys: pytest.CaptureFixture):
     Path(temp_template.name).unlink()
 
 
-@pytest.mark.usefixtures("sample_job", "sample_step_map", "patched_session_cleanup", "capsys")
+@pytest.mark.usefixtures("sample_job_and_dirs", "sample_step_map", "patched_session_cleanup", "capsys")
 @pytest.mark.parametrize(
     "step_index,dependency_indexes,should_run_dependencies",
     [
@@ -226,7 +226,7 @@ def test_do_run_nonexistent_step(capsys: pytest.CaptureFixture):
     ],
 )
 def test_run_local_session_success(
-    sample_job: Job,
+    sample_job_and_dirs: tuple,
     sample_step_map: dict,
     patched_session_cleanup: Mock,
     capsys: pytest.CaptureFixture,
@@ -240,6 +240,7 @@ def test_run_local_session_success(
     Note that we don't need to test with custom Task parameters, as those are
     tested within the `LocalSession` object.
     """
+    sample_job, template_dir, current_working_dir = sample_job_and_dirs
     path_mapping_rules = [
         PathMappingRule(
             source_path_format=PathFormat.WINDOWS,
@@ -273,7 +274,7 @@ def test_run_local_session_success(
     patched_session_cleanup.assert_called()
 
 
-@pytest.mark.usefixtures("sample_job", "sample_step_map")
+@pytest.mark.usefixtures("sample_job_and_dirs", "sample_step_map")
 @pytest.mark.parametrize(
     "step_index,should_run_dependencies,expected_error",
     [
@@ -289,7 +290,7 @@ def test_run_local_session_success(
     ],
 )
 def test_run_local_session_failed(
-    sample_job: Job,
+    sample_job_and_dirs: tuple,
     sample_step_map: dict,
     step_index: int,
     should_run_dependencies: bool,
@@ -298,6 +299,7 @@ def test_run_local_session_failed(
     """
     Test the output of a Session that finishes after encountering errors.
     """
+    sample_job, template_dir, current_working_dir = sample_job_and_dirs
     response = _run_local_session(
         job=sample_job,
         step_map=sample_step_map,