diff --git a/jira/resources.py b/jira/resources.py
index 29c86e604..d70c498db 100644
--- a/jira/resources.py
+++ b/jira/resources.py
@@ -11,6 +11,7 @@
 import re
 import time
 from typing import TYPE_CHECKING, Any, cast
+from urllib.parse import ParseResult, urlparse, urlunparse
 
 from requests import Response
 from requests.structures import CaseInsensitiveDict
@@ -292,6 +293,24 @@ def _get_url(self, path: str) -> str:
         options.update({"path": path})
         return self._base_url.format(**options)
 
+    def _validate_self_self_url(self) -> None:
+        """In the case of a proxy, use the configured option server URL."""
+        if getattr(self, "self", None):
+            self.self: str
+            self_parsed = urlparse(self.self)
+            server_parsed = urlparse(self._options["server"])
+            if self_parsed.netloc != server_parsed.netloc:
+                self.self = urlunparse(
+                    ParseResult(
+                        scheme=server_parsed.scheme,
+                        netloc=server_parsed.netloc,
+                        path=self_parsed.path,
+                        params=self_parsed.params,
+                        query=self_parsed.query,
+                        fragment=self_parsed.fragment,
+                    )
+                )
+
     def update(
         self,
         fields: dict[str, Any] | None = None,
@@ -326,6 +345,7 @@ def update(
         else:
             querystring = ""
 
+        self._validate_self_self_url()
         r = self._session.put(self.self + querystring, data=json.dumps(data))
         if "autofix" in self._options and r.status_code == 400:
             user = None
@@ -420,6 +440,7 @@ def delete(self, params: dict[str, Any] | None = None) -> Response | None:
         Returns:
             Optional[Response]: Returns None if async
         """
+        self._validate_self_self_url()
         if self._options["async"]:
             # FIXME: mypy doesn't think this should work
             if not hasattr(self._session, "_async_jobs"):
@@ -1504,7 +1525,7 @@ def __init__(
         session: ResilientSession,
         raw: dict[str, Any] | None = None,
     ):
-        self.self = None
+        self.self = ""
 
         Resource.__init__(self, path, options, session, self.AGILE_BASE_URL)
         if raw:
diff --git a/tests/resources/test_issue.py b/tests/resources/test_issue.py
index a496edb2e..27d3d67cd 100644
--- a/tests/resources/test_issue.py
+++ b/tests/resources/test_issue.py
@@ -337,6 +337,22 @@ def test_update_with_label(self):
         issue.update(fields=fields)
         self.assertEqual(issue.fields.labels, ["testLabel"])
 
+    def test_update_label_with_proxy(self):
+        issue = self.jira.create_issue(
+            summary="Test issue for updating labels",
+            project=self.project_b,
+            description="Label testing",
+            issuetype=self.test_manager.CI_JIRA_ISSUE,
+        )
+
+        labelarray = ["testLabel"]
+        fields = {"labels": labelarray}
+        # This simulates when your Jira server is behind a proxy
+        # The self address returned will be different from the configured server
+        issue.self = f"https://foo.bar/jira/rest/api/2/issue/{issue.id}"
+        issue.update(fields=fields)
+        self.assertEqual(issue.fields.labels, ["testLabel"])
+
     def test_update_with_bad_label(self):
         issue = self.jira.create_issue(
             summary="Test issue for updating bad labels",
@@ -373,6 +389,20 @@ def test_delete(self):
         issue.delete()
         self.assertRaises(JIRAError, self.jira.issue, key)
 
+    def test_delete_with_proxy(self):
+        issue = self.jira.create_issue(
+            summary="Test issue created",
+            project=self.project_b,
+            description="Not long for this world",
+            issuetype=self.test_manager.CI_JIRA_ISSUE,
+        )
+        key = issue.key
+        # This simulates when your Jira server is behind a proxy
+        # The self address returned will be different from the configured server
+        issue.self = f"https://foo.bar/jira/rest/api/2/issue/{issue.id}"
+        issue.delete()
+        self.assertRaises(JIRAError, self.jira.issue, key)
+
     def test_createmeta(self):
         meta = self.jira.createmeta()
         proj = find_by_key(meta["projects"], self.project_b)