diff --git a/changes-entries/setenvif-expr-stale-value.txt b/changes-entries/setenvif-expr-stale-value.txt
new file mode 100644
index 00000000000..fa4d4692bf0
--- /dev/null
+++ b/changes-entries/setenvif-expr-stale-value.txt
@@ -0,0 +1,3 @@
+  *) mod_setenvif: Fix a SetEnvIf rule being matched against the wrong
+     value when it follows a SetEnvIfExpr and an earlier rule for the same
+     header.  [arshiya tabasum <arshi bugqore.com>]
diff --git a/modules/metadata/mod_setenvif.c b/modules/metadata/mod_setenvif.c
index 87f11dd4ce4..aa1173d7a3e 100644
--- a/modules/metadata/mod_setenvif.c
+++ b/modules/metadata/mod_setenvif.c
@@ -602,6 +602,13 @@ static int match_headers(request_rec *r)
             }
 
         }
+        else {
+            /* ap_expr_exec_re() below may point val at the string its
+             * regex matched, so the next header rule must look up its
+             * value again rather than reuse val and val_len.
+             */
+            last_name = NULL;
+        }
 
         /*
          * A NULL value indicates that the header field or special entity
diff --git a/test/modules/metadata/test_005_setenvif.py b/test/modules/metadata/test_005_setenvif.py
new file mode 100644
index 00000000000..3cc55c476f9
--- /dev/null
+++ b/test/modules/metadata/test_005_setenvif.py
@@ -0,0 +1,50 @@
+import os
+
+import pytest
+
+from pyhttpd.conf import HttpdConf
+
+
+class TestSetEnvIf:
+
+    @pytest.fixture(autouse=True, scope='class')
+    def _class_scope(self, env):
+        doc_dir = os.path.join(env.server_dir, "htdocs", "test1")
+        os.makedirs(doc_dir, exist_ok=True)
+        with open(os.path.join(doc_dir, "setenvif.shtml"), "w") as f:
+            for name in ["SEI_FIRST", "SEI_EXPR", "SEI_LITERAL", "SEI_REGEX"]:
+                f.write(f'{name}=[<!--#echo var="{name}" -->]\n')
+        # Two rules on the same header with a SetEnvIfExpr between them:
+        # the second X-A rule must still be matched against X-A, not
+        # against the string the expression's regex was applied to.
+        conf = HttpdConf(env, extras={
+            'base': f"""
+            SetEnvIf X-A foo SEI_FIRST=1
+            SetEnvIfExpr "req('X-B') =~ /(.+)/" SEI_EXPR=$1
+            SetEnvIf X-A bar SEI_LITERAL=1
+            SetEnvIf X-A ^bar$ SEI_REGEX=1
+            <Directory "{doc_dir}">
+                Options +Includes
+                AddType text/html .shtml
+                AddOutputFilter INCLUDES .shtml
+            </Directory>
+            """,
+        })
+        conf.add_vhost_test1()
+        conf.install()
+        assert env.apache_restart() == 0
+
+    def test_metadata_005_01_expr_between_header_rules(self, env):
+        url = env.mkurl("http", "test1", "/setenvif.shtml")
+        r = env.curl_get(url, options=[
+            "-H", "X-A: foo-" + "x" * 64,
+            "-H", "X-B: bar",
+        ])
+        assert r.response, "no response: server may have crashed"
+        assert r.response["status"] == 200
+        body = r.response["body"].decode("utf-8")
+        assert "SEI_FIRST=[1]" in body
+        assert "SEI_EXPR=[bar]" in body
+        # X-A does not contain "bar", only X-B does
+        assert "SEI_LITERAL=[(none)]" in body
+        assert "SEI_REGEX=[(none)]" in body