diff --git a/providers/ssh/src/airflow/providers/ssh/operators/ssh_remote_job.py b/providers/ssh/src/airflow/providers/ssh/operators/ssh_remote_job.py
index 7c126c7c6e7d2..fec1be1536913 100644
--- a/providers/ssh/src/airflow/providers/ssh/operators/ssh_remote_job.py
+++ b/providers/ssh/src/airflow/providers/ssh/operators/ssh_remote_job.py
@@ -452,9 +452,9 @@ def _cleanup_remote_job(self, job_dir: str, remote_os: str) -> None:
         """
         self.log.info("Cleaning up remote job directory: %s", job_dir)
         if remote_os == "posix":
-            cleanup_cmd = build_posix_cleanup_command(job_dir)
+            cleanup_cmd = build_posix_cleanup_command(job_dir, base_dir=self.remote_base_dir)
         else:
-            cleanup_cmd = build_windows_cleanup_command(job_dir)
+            cleanup_cmd = build_windows_cleanup_command(job_dir, base_dir=self.remote_base_dir)
 
         last_error: Exception | None = None
         for attempt in range(1, self.cleanup_retries + 1):
diff --git a/providers/ssh/src/airflow/providers/ssh/utils/remote_job.py b/providers/ssh/src/airflow/providers/ssh/utils/remote_job.py
index d8d7d8ff3fd59..5cc0699322ed0 100644
--- a/providers/ssh/src/airflow/providers/ssh/utils/remote_job.py
+++ b/providers/ssh/src/airflow/providers/ssh/utils/remote_job.py
@@ -30,23 +30,26 @@
 WINDOWS_DEFAULT_BASE_DIR = "$env:TEMP\\airflow-ssh-jobs"
 
 
-def _validate_job_dir(job_dir: str, remote_os: Literal["posix", "windows"]) -> None:
+def _validate_job_dir(
+    job_dir: str, remote_os: Literal["posix", "windows"], base_dir: str | None = None
+) -> None:
     """
     Validate that job_dir is under the expected base directory.
 
     :param job_dir: The job directory path to validate
     :param remote_os: Operating system type
+    :param base_dir: The base directory job_dir is expected to be under. Defaults to the
+        standard POSIX/Windows base directory, but callers configured with a custom
+        ``remote_base_dir`` must pass it here so job_dir is validated against the base
+        directory that was actually used to build it.
     :raises ValueError: If job_dir doesn't start with the expected base path
     """
-    if remote_os == "posix":
-        expected_prefix = POSIX_DEFAULT_BASE_DIR + "/"
-    else:
-        expected_prefix = WINDOWS_DEFAULT_BASE_DIR + "\\"
+    if base_dir is None:
+        base_dir = POSIX_DEFAULT_BASE_DIR if remote_os == "posix" else WINDOWS_DEFAULT_BASE_DIR
+    expected_prefix = base_dir + ("\\" if remote_os == "windows" else "/")
 
     if not job_dir.startswith(expected_prefix):
-        raise ValueError(
-            f"Invalid job directory '{job_dir}'. Expected path under '{expected_prefix[:-1]}' for safety."
-        )
+        raise ValueError(f"Invalid job directory '{job_dir}'. Expected path under '{base_dir}' for safety.")
 
 
 def _validate_env_var_name(name: str) -> None:
@@ -456,27 +459,31 @@ def build_windows_kill_command(pid_file: str) -> str:
     return f"powershell.exe -NoProfile -NonInteractive -EncodedCommand {encoded_script}"
 
 
-def build_posix_cleanup_command(job_dir: str) -> str:
+def build_posix_cleanup_command(job_dir: str, base_dir: str | None = None) -> str:
     """
     Build a POSIX command to clean up the job directory.
 
     :param job_dir: Path to the job directory
+    :param base_dir: The configured base directory job_dir is expected to be under
+        (see :func:`_validate_job_dir`). Defaults to the standard base directory.
     :return: Shell command to remove the directory
     :raises ValueError: If job_dir is not under the expected base directory
     """
-    _validate_job_dir(job_dir, "posix")
+    _validate_job_dir(job_dir, "posix", base_dir=base_dir)
     return f"rm -rf '{job_dir}'"
 
 
-def build_windows_cleanup_command(job_dir: str) -> str:
+def build_windows_cleanup_command(job_dir: str, base_dir: str | None = None) -> str:
     """
     Build a PowerShell command to clean up the job directory.
 
     :param job_dir: Path to the job directory
+    :param base_dir: The configured base directory job_dir is expected to be under
+        (see :func:`_validate_job_dir`). Defaults to the standard base directory.
     :return: PowerShell command to remove the directory
     :raises ValueError: If job_dir is not under the expected base directory
     """
-    _validate_job_dir(job_dir, "windows")
+    _validate_job_dir(job_dir, "windows", base_dir=base_dir)
     escaped_path = job_dir.replace("'", "''")
     script = f"Remove-Item -Recurse -Force -Path '{escaped_path}' -ErrorAction SilentlyContinue"
     script_bytes = script.encode("utf-16-le")
diff --git a/providers/ssh/tests/unit/ssh/operators/test_ssh_remote_job.py b/providers/ssh/tests/unit/ssh/operators/test_ssh_remote_job.py
index 55e144bab2727..ceb5511d30811 100644
--- a/providers/ssh/tests/unit/ssh/operators/test_ssh_remote_job.py
+++ b/providers/ssh/tests/unit/ssh/operators/test_ssh_remote_job.py
@@ -393,6 +393,43 @@ def test_execute_complete_with_cleanup(self):
         call_args = self.mock_hook.exec_ssh_client_command.call_args
         assert "rm -rf" in call_args[0][1]
 
+    def test_execute_complete_with_cleanup_and_custom_remote_base_dir(self):
+        """
+        Cleanup must validate job_dir against the operator's configured
+        remote_base_dir, not the hardcoded default. Regression test for a bug
+        where a custom remote_base_dir made execution/monitoring succeed but
+        cleanup always raised ValueError, since it only accepted job_dir under
+        the default base directory.
+        """
+        op = SSHRemoteJobOperator(
+            task_id="test_task",
+            ssh_conn_id="test_conn",
+            command="/path/to/script.sh",
+            cleanup="on_success",
+            remote_base_dir="/opt/custom-airflow-jobs",
+        )
+        op.remote_base_dir = "/opt/custom-airflow-jobs"  # post-templating value
+
+        event = {
+            "done": True,
+            "status": "success",
+            "exit_code": 0,
+            "job_id": "test_job_123",
+            "job_dir": "/opt/custom-airflow-jobs/test_job_123",
+            "log_file": "/opt/custom-airflow-jobs/test_job_123/stdout.log",
+            "exit_code_file": "/opt/custom-airflow-jobs/test_job_123/exit_code",
+            "log_chunk": "",
+            "log_offset": 0,
+            "remote_os": "posix",
+        }
+
+        op.execute_complete({}, event)
+
+        self.mock_hook.exec_ssh_client_command.assert_called_once()
+        call_args = self.mock_hook.exec_ssh_client_command.call_args
+        assert "rm -rf" in call_args[0][1]
+        assert "/opt/custom-airflow-jobs/test_job_123" in call_args[0][1]
+
     def test_on_kill(self):
         """Test on_kill attempts to kill remote process."""
         op = SSHRemoteJobOperator(
diff --git a/providers/ssh/tests/unit/ssh/utils/test_remote_job.py b/providers/ssh/tests/unit/ssh/utils/test_remote_job.py
index 53c1f6f80b455..2dadebaa366dd 100644
--- a/providers/ssh/tests/unit/ssh/utils/test_remote_job.py
+++ b/providers/ssh/tests/unit/ssh/utils/test_remote_job.py
@@ -453,3 +453,18 @@ def test_windows_cleanup_rejects_invalid_path(self):
         """Test Windows cleanup rejects paths outside expected base directory."""
         with pytest.raises(ValueError, match="Invalid job directory"):
             build_windows_cleanup_command("C:\\temp\\other_dir")
+
+    def test_posix_cleanup_accepts_custom_base_dir(self):
+        """Cleanup must validate against the base_dir that was actually configured."""
+        cmd = build_posix_cleanup_command("/custom/base/job_123", base_dir="/custom/base")
+        assert "/custom/base/job_123" in cmd
+
+    def test_posix_cleanup_rejects_default_dir_when_custom_base_dir_configured(self):
+        """A job_dir under the default base must not pass when a custom base_dir was used."""
+        with pytest.raises(ValueError, match="Invalid job directory"):
+            build_posix_cleanup_command("/tmp/airflow-ssh-jobs/job_123", base_dir="/custom/base")
+
+    def test_windows_cleanup_accepts_custom_base_dir(self):
+        """Cleanup must validate against the base_dir that was actually configured."""
+        cmd = build_windows_cleanup_command("C:\\custom\\base\\job_123", base_dir="C:\\custom\\base")
+        assert "powershell.exe" in cmd