diff --git a/changelog.d/1389.bugfix.md b/changelog.d/1389.bugfix.md
new file mode 100644
index 0000000000..a290ff8370
--- /dev/null
+++ b/changelog.d/1389.bugfix.md
@@ -0,0 +1 @@
+Fix passing constraints file path into `pipx install` operation via `pip` args
diff --git a/src/pipx/main.py b/src/pipx/main.py
index 5f2d20c09c..79f55516f5 100644
--- a/src/pipx/main.py
+++ b/src/pipx/main.py
@@ -159,7 +159,9 @@ def get_pip_args(parsed_args: Dict[str, str]) -> List[str]:
         pip_args += ["--index-url", parsed_args["index_url"]]
 
     if parsed_args.get("pip_args"):
-        pip_args += shlex.split(parsed_args.get("pip_args", ""), posix=not WINDOWS)
+        # Stripping the single quote that can be parsed from several shells
+        pip_args_striped = parsed_args["pip_args"].strip("'")
+        pip_args += shlex.split(pip_args_striped, posix=not WINDOWS)
 
     # make sure --editable is last because it needs to be right before
     #   package specification
diff --git a/src/pipx/package_specifier.py b/src/pipx/package_specifier.py
index 62fe053195..066a6b31fc 100644
--- a/src/pipx/package_specifier.py
+++ b/src/pipx/package_specifier.py
@@ -163,7 +163,27 @@ def parse_specifier_for_install(package_spec: str, pip_args: List[str]) -> Tuple
         )
         pip_args.remove("--editable")
 
-    return (package_or_url, pip_args)
+    for index, option in enumerate(pip_args):
+        if not option.startswith(("-c", "--constraint")):
+            continue
+
+        if option in ("-c", "--constraint"):
+            argument_index = index + 1
+            if argument_index < len(pip_args):
+                constraints_file = pip_args[argument_index]
+                pip_args[argument_index] = str(Path(constraints_file).expanduser().resolve())
+
+        else:  # option == "--constraint=some_path"
+            option_list = option.split("=")
+
+            if len(option_list) == 2:
+                key, value = option_list
+                value_path = Path(value).expanduser().resolve()
+                pip_args[index] = f"{key}={value_path}"
+
+        break
+
+    return package_or_url, pip_args
 
 
 def parse_specifier_for_metadata(package_spec: str) -> str:
diff --git a/tests/test_install.py b/tests/test_install.py
index a4fc3b29f7..b83310e988 100644
--- a/tests/test_install.py
+++ b/tests/test_install.py
@@ -264,6 +264,39 @@ def test_pip_args_with_windows_path(pipx_temp_env, capsys):
     assert r"D:\\TEST\\DIR" in captured.err
 
 
+@pytest.mark.parametrize("constraint_flag", ["-c ", "--constraint ", "--constraint="])
+def test_pip_args_with_constraint_relative_path(constraint_flag, pipx_temp_env, tmp_path, caplog):
+    constraint_file_name = "constraints.txt"
+    package_name = "ipython"
+    package_version = "8.23.0"
+
+    os.chdir(tmp_path)
+    constraints_file = tmp_path / constraint_file_name
+    constraints_file.write_text(f"{package_name}!={package_version}")
+    constraints_file.touch()
+
+    assert not run_pipx_cli(["install", f"--pip-args='{constraint_flag}{constraint_file_name}'", package_name])
+
+    assert f"{constraint_flag}{constraints_file}" in caplog.text
+
+    subprocess_package_version = subprocess.run([package_name, "--version"], capture_output=True, text=True, check=False)
+    subprocess_package_version_output = subprocess_package_version.stdout.strip()
+    assert subprocess_package_version_output != package_version
+
+
+@pytest.mark.parametrize("constraint_flag", ["-c ", "--constraint ", "--constraint="])
+def test_pip_args_with_wrong_constraint_fail(constraint_flag, pipx_ultra_temp_env, tmp_path, capsys):
+    constraint_file_name = "constraints.txt"
+    os.chdir(tmp_path)
+
+    assert run_pipx_cli(["install", f"--pip-args='{constraint_flag}{constraint_file_name}'", "pycowsay"])
+
+    assert (
+        f"ERROR: Could not open requirements file: [Errno 2] No such file or directory: '{constraint_file_name}'"
+        in capsys.readouterr().err
+    )
+
+
 def test_install_suffix(pipx_temp_env, capsys):
     name = "pbr"