diff --git a/pyproject.toml b/pyproject.toml
index 1f296839..b06efc77 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -102,7 +102,6 @@ select = [
 ]
 extend-ignore = [
   "A003",  # builtin-attribute-shadowing
-  "B028",  # no-explicit-stacklevel
   "C408",  # unnecessary-collection-call
   "ISC003",  # explicit-string-concatenation
   "PLC1901",  # compare-to-empty-string
diff --git a/src/streamlink/options.py b/src/streamlink/options.py
index 00ef5d6d..58d2d446 100644
--- a/src/streamlink/options.py
+++ b/src/streamlink/options.py
@@ -136,6 +136,9 @@ class Argument:
             warnings.warn(
                 "Defining global plugin arguments is deprecated. Use the session options instead.",
                 StreamlinkDeprecationWarning,
+                # set stacklevel to 3 because of the @pluginargument decorator
+                # which is the public interface for defining plugin arguments
+                stacklevel=3,
             )
 
     @staticmethod
diff --git a/src/streamlink/plugin/api/validate/__init__.py b/src/streamlink/plugin/api/validate/__init__.py
index 36898153..ead3fe3d 100644
--- a/src/streamlink/plugin/api/validate/__init__.py
+++ b/src/streamlink/plugin/api/validate/__init__.py
@@ -64,7 +64,7 @@ def _deprecations():
             from streamlink.exceptions import StreamlinkDeprecationWarning
 
             val, msg = deprecations[_attr]
-            warnings.warn(msg, StreamlinkDeprecationWarning)
+            warnings.warn(msg, StreamlinkDeprecationWarning, stacklevel=2)
 
             return val
 
diff --git a/src/streamlink/plugin/plugin.py b/src/streamlink/plugin/plugin.py
index 0af787f2..3c54ed9d 100644
--- a/src/streamlink/plugin/plugin.py
+++ b/src/streamlink/plugin/plugin.py
@@ -306,6 +306,7 @@ class Plugin:
                 warnings.warn(
                     f"Initialized {self.module} plugin with deprecated constructor",
                     FutureWarning,
+                    stacklevel=2,
                 )
 
         # Wrapper class which comes after the deprecated plugin in the MRO
diff --git a/src/streamlink/session.py b/src/streamlink/session.py
index 9f2f6d23..bc55e8da 100644
--- a/src/streamlink/session.py
+++ b/src/streamlink/session.py
@@ -27,6 +27,21 @@ log = logging.getLogger(__name__)
 _original_allowed_gai_family = urllib3_util_connection.allowed_gai_family  # type: ignore[attr-defined]
 
 
+def _get_deprecation_stacklevel_offset():
+    """Deal with stacklevels of both session.{g,s}et_option() and session.options.{g,s}et() calls"""
+    from inspect import currentframe
+
+    frame = currentframe().f_back.f_back
+    offset = 0
+    while frame:
+        if frame.f_code.co_filename == __file__ and frame.f_code.co_name in ("set_option", "get_option"):
+            offset += 1
+            break
+        frame = frame.f_back
+
+    return offset
+
+
 class PythonDeprecatedWarning(UserWarning):
     pass
 
@@ -47,14 +62,19 @@ class StreamlinkOptions(Options):
             except ValueError:
                 continue
 
-    # ---- getters
-
-    def _get_http_proxy(self, key):
+    @staticmethod
+    def _deprecate_https_proxy(key: str) -> None:
         if key == "https-proxy":
             warnings.warn(
                 "The `https-proxy` option has been deprecated in favor of a single `http-proxy` option",
                 StreamlinkDeprecationWarning,
+                stacklevel=4 + _get_deprecation_stacklevel_offset(),
             )
+
+    # ---- getters
+
+    def _get_http_proxy(self, key):
+        self._deprecate_https_proxy(key)
         return self.session.http.proxies.get("https" if key == "https-proxy" else "http")
 
     def _get_http_attr(self, key):
@@ -88,11 +108,7 @@ class StreamlinkOptions(Options):
         self.session.http.proxies["http"] \
             = self.session.http.proxies["https"] \
             = update_scheme("https://", value, force=False)
-        if key == "https-proxy":
-            warnings.warn(
-                "The `https-proxy` option has been deprecated in favor of a single `http-proxy` option",
-                StreamlinkDeprecationWarning,
-            )
+        self._deprecate_https_proxy(key)
 
     def _set_http_attr(self, key, value):
         setattr(self.session.http, self._OPTIONS_HTTP_ATTRS[key], value)
@@ -124,6 +140,7 @@ class StreamlinkOptions(Options):
             warnings.warn(
                 f"`{key}` has been deprecated in favor of the `{name}` option",
                 StreamlinkDeprecationWarning,
+                stacklevel=3 + _get_deprecation_stacklevel_offset(),
             )
 
         return inner
@@ -547,6 +564,7 @@ class Streamlink:
                     warnings.warn(
                         f"Resolved plugin {name} with deprecated can_handle_url API",
                         StreamlinkDeprecationWarning,
+                        stacklevel=1,
                     )
                     candidate = name, plugin
                     priority = prio
diff --git a/src/streamlink_cli/main.py b/src/streamlink_cli/main.py
index 88f9bd57..f420f8d8 100644
--- a/src/streamlink_cli/main.py
+++ b/src/streamlink_cli/main.py
@@ -610,6 +610,7 @@ def load_plugins(dirs: List[Path], showwarning: bool = True):
                 warnings.warn(
                     f"Loaded plugins from deprecated path, see CLI docs for how to migrate: {directory}",
                     StreamlinkDeprecationWarning,
+                    stacklevel=1,
                 )
         elif showwarning:
             log.warning(f"Plugin path {directory} does not exist or is not a directory!")
@@ -658,6 +659,7 @@ def setup_config_args(parser, ignore_unknown=False):
                 warnings.warn(
                     f"Loaded config from deprecated path, see CLI docs for how to migrate: {config_file}",
                     StreamlinkDeprecationWarning,
+                    stacklevel=1,
                 )
             config_files.append(config_file)
             break
@@ -674,6 +676,7 @@ def setup_config_args(parser, ignore_unknown=False):
                     warnings.warn(
                         f"Loaded plugin config from deprecated path, see CLI docs for how to migrate: {config_file}",
                         StreamlinkDeprecationWarning,
+                        stacklevel=1,
                     )
                 config_files.append(config_file)
                 break
diff --git a/tests/test_api_validate.py b/tests/test_api_validate.py
index bd4521a3..38b9ca3b 100644
--- a/tests/test_api_validate.py
+++ b/tests/test_api_validate.py
@@ -19,10 +19,11 @@ def test_text_is_str(recwarn: pytest.WarningsRecorder):
     assert "text" not in getattr(validate, "__dict__", {})
     assert "text" in getattr(validate, "__all__", [])
     assert validate.text is str, "Exports text as str alias for backwards compatiblity"
-    assert [(record.category, str(record.message)) for record in recwarn.list] == [
+    assert [(record.category, str(record.message), record.filename) for record in recwarn.list] == [
         (
             StreamlinkDeprecationWarning,
             "`streamlink.plugin.api.validate.text` is deprecated. Use `str` instead.",
+            __file__,
         ),
     ]
 
diff --git a/tests/test_options.py b/tests/test_options.py
index 2c4bc736..8a943247 100644
--- a/tests/test_options.py
+++ b/tests/test_options.py
@@ -242,8 +242,12 @@ class TestSetupOptions:
             def _get_streams(self):  # pragma: no cover
                 pass
 
-        assert [(record.category, str(record.message)) for record in recwarn.list] == [
-            (StreamlinkDeprecationWarning, "Defining global plugin arguments is deprecated. Use the session options instead."),
+        assert [(record.category, str(record.message), record.filename) for record in recwarn.list] == [
+            (
+                StreamlinkDeprecationWarning,
+                "Defining global plugin arguments is deprecated. Use the session options instead.",
+                __file__,
+            ),
         ]
 
         session = Mock()
diff --git a/tests/test_plugin.py b/tests/test_plugin.py
index 59521f95..628f7565 100644
--- a/tests/test_plugin.py
+++ b/tests/test_plugin.py
@@ -85,8 +85,12 @@ class TestPlugin:
 
         assert isinstance(plugin, DeprecatedPlugin)
         assert plugin.custom_attribute == "HTTP://LOCALHOST"
-        assert [(record.category, str(record.message)) for record in recwarn.list] == [
-            (FutureWarning, "Initialized test_plugin plugin with deprecated constructor"),
+        assert [(record.category, str(record.message), record.filename) for record in recwarn.list] == [
+            (
+                FutureWarning,
+                "Initialized test_plugin plugin with deprecated constructor",
+                __file__,
+            ),
         ]
 
         assert plugin.session is session
diff --git a/tests/test_session.py b/tests/test_session.py
index 7fa1dfdd..116854d9 100644
--- a/tests/test_session.py
+++ b/tests/test_session.py
@@ -10,9 +10,9 @@ import requests_mock
 import urllib3
 
 import tests.plugin
-from streamlink import NoPluginError, Streamlink
-from streamlink.exceptions import StreamlinkDeprecationWarning
+from streamlink.exceptions import NoPluginError, StreamlinkDeprecationWarning
 from streamlink.plugin import HIGH_PRIORITY, LOW_PRIORITY, NO_PRIORITY, NORMAL_PRIORITY, Plugin, pluginmatcher
+from streamlink.session import Streamlink
 from streamlink.stream.hls import HLSStream
 from streamlink.stream.http import HTTPStream
 
@@ -418,10 +418,11 @@ class TestSessionOptionHttpProxy:
     @pytest.fixture()
     def _logs_deprecation(self, recwarn: pytest.WarningsRecorder):
         yield
-        assert [(record.category, str(record.message)) for record in recwarn.list] == [
+        assert [(record.category, str(record.message), record.filename) for record in recwarn.list] == [
             (
                 StreamlinkDeprecationWarning,
                 "The `https-proxy` option has been deprecated in favor of a single `http-proxy` option",
+                __file__,
             ),
         ]
 
@@ -481,6 +482,16 @@ class TestSessionOptionHttpProxy:
         session.http.proxies["https"] = "http://testproxy2.com"
         assert session.get_option("https-proxy") == "http://testproxy2.com"
 
+    @pytest.mark.usefixtures("_logs_deprecation")
+    def test_https_proxy_get_directly(self, session: Streamlink):
+        # The DeprecationWarning's origin must point to this call, even without the set_option() wrapper
+        session.options.get("https-proxy")
+
+    @pytest.mark.usefixtures("_logs_deprecation")
+    def test_https_proxy_set_directly(self, session: Streamlink):
+        # The DeprecationWarning's origin must point to this call, even without the set_option() wrapper
+        session.options.set("https-proxy", "https://foo")
+
 
 class TestOptionsKeyEqualsValue:
     @pytest.fixture()