diff --git a/hatch.toml b/hatch.toml
index 0d114924..de700728 100644
--- a/hatch.toml
+++ b/hatch.toml
@@ -13,6 +13,7 @@ version = "hatch version"
 metadata = "hatch project metadata {args:}"
 linux-e2e-test = "pytest --no-cov test/e2e/linux {args}"
 windows-e2e-test= "pytest --no-cov test/e2e/windows {args:}"
+cross-os-e2e-test = "pytest --no-cov test/e2e/cross_os {args}"
 windows-integ-test = "pytest --no-cov test/integ/installer {args:}"
 typing = "mypy {args:src test}"
 style = [
diff --git a/pipeline/e2e.sh b/pipeline/e2e.sh
index 5c6329cc..31cc00f1 100755
--- a/pipeline/e2e.sh
+++ b/pipeline/e2e.sh
@@ -24,4 +24,6 @@ fi
 if [ "$OPERATING_SYSTEM" = "windows" ]
   then
     hatch run windows-e2e-test
-fi
\ No newline at end of file
+fi
+
+hatch run cross-os-e2e-test
\ No newline at end of file
diff --git a/requirements-testing.txt b/requirements-testing.txt
index ebe05a5d..2b9f3527 100644
--- a/requirements-testing.txt
+++ b/requirements-testing.txt
@@ -1,3 +1,4 @@
+backoff == 2.2.*
 coverage[toml] ~= 7.5
 coverage-conditional-plugin == 0.9.*
 deadline-cloud-test-fixtures == 0.12.*
diff --git a/test/e2e/cross_os/test_job_submissions.py b/test/e2e/cross_os/test_job_submissions.py
new file mode 100644
index 00000000..3bcd10dc
--- /dev/null
+++ b/test/e2e/cross_os/test_job_submissions.py
@@ -0,0 +1,372 @@
+# Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+"""
+This test module contains tests that verify the Worker agent's behavior by submitting jobs to the
+Deadline Cloud service and checking that the result/output of the jobs is as we expect it.
+"""
+from typing import Any, Dict, List
+import pytest
+import logging
+from deadline_test_fixtures import Job, DeadlineClient, TaskStatus
+from utils import get_operating_system_name
+import backoff
+import boto3
+import botocore.client
+import botocore.config
+import botocore.exceptions
+
+LOG = logging.getLogger(__name__)
+
+
+@pytest.mark.usefixtures("worker")
+@pytest.mark.parametrize("operating_system", [get_operating_system_name()], indirect=True)
+class TestJobSubmission:
+    @pytest.mark.parametrize(
+        "run_actions,environment_actions, expected_failed_action",
+        [
+            (
+                {
+                    "onRun": {
+                        "command": "noneexistentcommand",  # This will fail
+                    },
+                },
+                {
+                    "onEnter": {
+                        "command": "whoami",
+                    },
+                },
+                "taskRun",
+            ),
+            (
+                {
+                    "onRun": {
+                        "command": "whoami",
+                    },
+                },
+                {
+                    "onEnter": {
+                        "command": "noneexistentcommand",  # This will fail
+                    },
+                },
+                "envEnter",
+            ),
+            (
+                {
+                    "onRun": {
+                        "command": "whoami",
+                    },
+                },
+                {
+                    "onEnter": {
+                        "command": "whoami",
+                    },
+                    "onExit": {
+                        "command": "noneexistentcommand",  # This will fail
+                    },
+                },
+                "envExit",
+            ),
+        ],
+    )
+    def test_job_reports_failed_session_action(
+        self,
+        deadline_resources,
+        deadline_client: DeadlineClient,
+        run_actions: Dict[str, Any],
+        environment_actions: Dict[str, Any],
+        expected_failed_action: str,
+    ) -> None:
+
+        job = Job.submit(
+            client=deadline_client,
+            farm=deadline_resources.farm,
+            queue=deadline_resources.queue_a,
+            priority=98,
+            template={
+                "specificationVersion": "jobtemplate-2023-09",
+                "name": f"jobactionfail-{expected_failed_action}",
+                "steps": [
+                    {
+                        "name": "Step0",
+                        "script": {"actions": run_actions},
+                    },
+                ],
+                "jobEnvironments": [
+                    {"name": "badenvironment", "script": {"actions": environment_actions}}
+                ],
+            },
+        )
+        # THEN
+        job.wait_until_complete(client=deadline_client)
+
+        # Retrieve job output and verify that the expected session action has failed
+
+        sessions = deadline_client.list_sessions(
+            farmId=job.farm.id, queueId=job.queue.id, jobId=job.id
+        ).get("sessions")
+        found_failed_session_action: bool = False
+        for session in sessions:
+            session_actions = deadline_client.list_session_actions(
+                farmId=job.farm.id,
+                queueId=job.queue.id,
+                jobId=job.id,
+                sessionId=session["sessionId"],
+            ).get("sessionActions")
+
+            for session_action in session_actions:
+                # Session action should be failed IFF it's the expected action to fail
+                if expected_failed_action in session_action["definition"]:
+                    found_failed_session_action = True
+                    assert session_action["status"] == "FAILED"
+                else:
+                    assert session_action["status"] != "FAILED"
+        assert found_failed_session_action
+
+    @pytest.mark.parametrize(
+        "run_actions,environment_actions,expected_canceled_action",
+        [
+            (
+                {
+                    "onRun": {
+                        "command": (
+                            "/bin/sleep" if get_operating_system_name() == "linux" else "timeout"
+                        ),
+                        "args": ["40"],
+                        "cancelation": {
+                            "mode": "NOTIFY_THEN_TERMINATE",
+                            "notifyPeriodInSeconds": 1,
+                        },
+                    },
+                },
+                {
+                    "onEnter": {
+                        "command": "whoami",
+                    },
+                },
+                "taskRun",
+            ),
+            (
+                {
+                    "onRun": {
+                        "command": "whoami",
+                    },
+                },
+                {
+                    "onEnter": {
+                        "command": (
+                            "/bin/sleep" if get_operating_system_name() == "linux" else "timeout"
+                        ),
+                        "args": ["40"],
+                        "cancelation": {
+                            "mode": "NOTIFY_THEN_TERMINATE",
+                            "notifyPeriodInSeconds": 1,
+                        },
+                    },
+                },
+                "envEnter",
+            ),
+        ],
+    )
+    def test_job_reports_canceled_session_action(
+        self,
+        deadline_resources,
+        deadline_client: DeadlineClient,
+        run_actions: Dict[str, Any],
+        environment_actions: Dict[str, Any],
+        expected_canceled_action: str,
+    ) -> None:
+        job = Job.submit(
+            client=deadline_client,
+            farm=deadline_resources.farm,
+            queue=deadline_resources.queue_a,
+            priority=98,
+            template={
+                "specificationVersion": "jobtemplate-2023-09",
+                "name": f"jobactioncancel-{expected_canceled_action}",
+                "steps": [
+                    {
+                        "name": "Step0",
+                        "script": {
+                            "actions": run_actions,
+                        },
+                    },
+                ],
+                "jobEnvironments": [
+                    {
+                        "name": "environment",
+                        "script": {
+                            "actions": environment_actions,
+                        },
+                    }
+                ],
+            },
+        )
+
+        @backoff.on_predicate(
+            wait_gen=backoff.constant,
+            max_time=120,
+            interval=10,
+        )
+        def is_job_started(current_job: Job) -> bool:
+            current_job.refresh_job_info(client=deadline_client)
+            LOG.info(f"Waiting for job {current_job.id} to be created")
+            return current_job.lifecycle_status != "CREATE_IN_PROGRESS"
+
+        assert is_job_started(job)
+
+        @backoff.on_predicate(
+            wait_gen=backoff.constant,
+            max_time=120,
+            interval=10,
+        )
+        def sessions_exist(current_job: Job) -> bool:
+            sessions = deadline_client.list_sessions(
+                farmId=current_job.farm.id, queueId=current_job.queue.id, jobId=current_job.id
+            ).get("sessions")
+
+            return len(sessions) > 0
+
+        assert sessions_exist(job)
+
+        deadline_client.update_job(
+            farmId=job.farm.id, queueId=job.queue.id, jobId=job.id, targetTaskRunStatus="CANCELED"
+        )
+
+        # THEN
+
+        # Wait until the job is canceled or completed
+        job.wait_until_complete(client=deadline_client)
+
+        LOG.info(f"Job result: {job}")
+
+        @backoff.on_predicate(
+            wait_gen=backoff.constant,
+            max_time=120,
+            interval=10,
+        )
+        def is_expected_session_action_canceled(sessions: List[Dict[str, Any]]) -> bool:
+            found_canceled_session_action: bool = False
+            for session in sessions:
+                session_actions = deadline_client.list_session_actions(
+                    farmId=job.farm.id,
+                    queueId=job.queue.id,
+                    jobId=job.id,
+                    sessionId=session["sessionId"],
+                ).get("sessionActions")
+
+                LOG.info(f"Session Actions: {session_actions}")
+                for session_action in session_actions:
+
+                    # Session action should be canceled if it's the action we expect to be canceled
+                    if expected_canceled_action in session_action["definition"]:
+                        if session_action["status"] == "CANCELED":
+                            found_canceled_session_action = True
+                    else:
+                        assert (
+                            session_action["status"] != "CANCELED"
+                        )  # This should not happen at all, so we fast exit
+            return found_canceled_session_action
+
+        sessions = deadline_client.list_sessions(
+            farmId=job.farm.id, queueId=job.queue.id, jobId=job.id
+        ).get("sessions")
+        assert is_expected_session_action_canceled(sessions)
+
+    @pytest.mark.parametrize(
+        "job_environments",
+        [
+            ([]),
+            (
+                [
+                    {
+                        "name": "environment_1",
+                        "script": {
+                            "actions": {
+                                "onEnter": {"command": "echo", "args": ["Hello!"]},
+                            },
+                        },
+                    },
+                ]
+            ),
+            (
+                [
+                    {
+                        "name": "environment_1",
+                        "script": {
+                            "actions": {
+                                "onEnter": {"command": "echo", "args": ["Hello!"]},
+                            }
+                        },
+                    },
+                    {
+                        "name": "environment_2",
+                        "script": {
+                            "actions": {
+                                "onEnter": {"command": "echo", "args": ["Hello!"]},
+                            }
+                        },
+                    },
+                    {
+                        "name": "environment_3",
+                        "script": {
+                            "actions": {
+                                "onEnter": {"command": "echo", "args": ["Hello!"]},
+                            }
+                        },
+                    },
+                ]
+            ),
+        ],
+    )
+    def test_worker_run_with_number_of_environments(
+        self,
+        deadline_resources,
+        deadline_client: DeadlineClient,
+        job_environments: List[Dict[str, Any]],
+    ) -> None:
+        job_template = {
+            "specificationVersion": "jobtemplate-2023-09",
+            "name": f"jobWithNumberOfEnvironments-{len(job_environments)}",
+            "steps": [
+                {
+                    "name": "Step0",
+                    "script": {
+                        "actions": {
+                            "onRun": {
+                                "command": "whoami",
+                            },
+                        },
+                    },
+                },
+            ],
+        }
+
+        if len(job_environments) > 0:
+            job_template["jobEnvironments"] = job_environments
+        job = Job.submit(
+            client=deadline_client,
+            farm=deadline_resources.farm,
+            queue=deadline_resources.queue_a,
+            priority=98,
+            template=job_template,
+        )
+
+        job.wait_until_complete(client=deadline_client)
+
+        # Retrieve job output and verify whoami printed the queue's jobsRunAsUser
+        job_logs = job.get_logs(
+            deadline_client=deadline_client,
+            logs_client=boto3.client(
+                "logs",
+                config=botocore.config.Config(retries={"max_attempts": 10, "mode": "adaptive"}),
+            ),
+        )
+
+        full_log = "\n".join(
+            [le.message for _, log_events in job_logs.logs.items() for le in log_events]
+        )
+
+        assert full_log.count("Hello!") == len(
+            job_environments
+        ), "Expected number of Hello statements not found in job logs."
+
+        assert job.task_run_status == TaskStatus.SUCCEEDED
diff --git a/test/e2e/cross_os/utils.py b/test/e2e/cross_os/utils.py
new file mode 100644
index 00000000..4a96e396
--- /dev/null
+++ b/test/e2e/cross_os/utils.py
@@ -0,0 +1,9 @@
+# Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+import sys
+
+
+def get_operating_system_name() -> str:
+    if sys.platform == "win32":
+        return "windows"
+    else:
+        return "linux"
diff --git a/test/e2e/linux/test_job_submissions.py b/test/e2e/linux/test_job_submissions.py
index bc0593cd..65f586dc 100644
--- a/test/e2e/linux/test_job_submissions.py
+++ b/test/e2e/linux/test_job_submissions.py
@@ -3,8 +3,6 @@
 This test module contains tests that verify the Worker agent's behavior by submitting jobs to the
 Deadline Cloud service and checking that the result/output of the jobs is as we expect it.
 """
-
-from typing import Any, Dict
 import boto3
 import botocore.client
 import botocore.config
@@ -111,108 +109,3 @@ def test_job_run_as_user(
             f"I am: {job_run_as_user.user}" in full_log
         ), f"Expected message not found in Job logs. Logs are in CloudWatch log group: {job_logs.log_group_name}"
         assert job.task_run_status == TaskStatus.SUCCEEDED
-
-    @pytest.mark.parametrize(
-        "run_actions,environment_actions, expected_failed_action",
-        [
-            (
-                {
-                    "onRun": {
-                        "command": "/bin/false",
-                        "args": ["1"],
-                    },
-                },
-                {
-                    "onEnter": {
-                        "command": "/bin/true",
-                    },
-                },
-                "taskRun",
-            ),
-            (
-                {
-                    "onRun": {
-                        "command": "/bin/sleep",
-                        "args": ["1"],
-                    },
-                },
-                {
-                    "onEnter": {
-                        "command": "/bin/false",
-                    },
-                },
-                "envEnter",
-            ),
-            (
-                {
-                    "onRun": {
-                        "command": "/bin/sleep",
-                        "args": ["1"],
-                    },
-                },
-                {
-                    "onEnter": {
-                        "command": "/bin/true",
-                    },
-                    "onExit": {
-                        "command": "/bin/false",
-                    },
-                },
-                "envExit",
-            ),
-        ],
-    )
-    def test_job_reports_failed_session_action(
-        self,
-        deadline_resources,
-        deadline_client: DeadlineClient,
-        run_actions: Dict[str, Any],
-        environment_actions: Dict[str, Any],
-        expected_failed_action: str,
-    ) -> None:
-
-        job = Job.submit(
-            client=deadline_client,
-            farm=deadline_resources.farm,
-            queue=deadline_resources.queue_a,
-            priority=98,
-            template={
-                "specificationVersion": "jobtemplate-2023-09",
-                "name": "environmentactionfail",
-                "steps": [
-                    {
-                        "name": "Step0",
-                        "script": {"actions": run_actions},
-                    },
-                ],
-                "jobEnvironments": [
-                    {"name": "badenvironment", "script": {"actions": environment_actions}}
-                ],
-            },
-        )
-        # THEN
-        job.wait_until_complete(client=deadline_client)
-
-        # Retrieve job output and verify that the expected session action has failed
-
-        sessions = deadline_client.list_sessions(
-            farmId=job.farm.id, queueId=job.queue.id, jobId=job.id
-        ).get("sessions")
-        found_failed_session_action: bool = False
-        for session in sessions:
-            session_actions = deadline_client.list_session_actions(
-                farmId=job.farm.id,
-                queueId=job.queue.id,
-                jobId=job.id,
-                sessionId=session["sessionId"],
-            ).get("sessionActions")
-
-            for session_action in session_actions:
-
-                # Session action should be failed IFF it's the expected action to fail
-                if expected_failed_action in session_action["definition"]:
-                    found_failed_session_action = True
-                    assert session_action["status"] == "FAILED"
-                else:
-                    assert session_action["status"] != "FAILED"
-        assert found_failed_session_action