diff --git a/ui/src/Stores/SilenceFormStore.js b/ui/src/Stores/SilenceFormStore.js
index 94754ec3f..232c16099 100644
--- a/ui/src/Stores/SilenceFormStore.js
+++ b/ui/src/Stores/SilenceFormStore.js
@@ -260,7 +260,19 @@ class SilenceFormStore {
         for (const m of silence.matchers) {
           const matcher = NewEmptyMatcher();
           matcher.name = m.name;
-          matcher.values = [MatcherValueToObject(m.value)];
+
+          if (m.isRegex && m.value.match(/^\((\w+\|)+\w+\)$/)) {
+            matcher.values = m.value
+              .slice(1, -1)
+              .split("|")
+              .map((v) => MatcherValueToObject(v));
+          } else if (m.isRegex && m.value.match(/^(\w+\|)+\w+$/)) {
+            matcher.values = m.value
+              .split("|")
+              .map((v) => MatcherValueToObject(v));
+          } else {
+            matcher.values = [MatcherValueToObject(m.value)];
+          }
           matcher.isRegex = m.isRegex;
           matchers.push(matcher);
         }
diff --git a/ui/src/Stores/SilenceFormStore.test.js b/ui/src/Stores/SilenceFormStore.test.js
index 5064b1f45..baf2954e5 100644
--- a/ui/src/Stores/SilenceFormStore.test.js
+++ b/ui/src/Stores/SilenceFormStore.test.js
@@ -315,6 +315,63 @@ describe("SilenceFormStore.data", () => {
     expect(store.data.comment).toBe("Mocked Silence");
   });
 
+  const tests = [
+    {
+      matcher: { name: "foo", value: "(bar1|bar2|bar3)", isRegex: true },
+      result: { name: "foo", values: ["bar1", "bar2", "bar3"] },
+    },
+    {
+      matcher: { name: "foo", value: "(bar1|bar2|bar3)", isRegex: false },
+      result: { name: "foo", values: ["(bar1|bar2|bar3)"] },
+    },
+    {
+      matcher: { name: "foo", value: "bar1|bar2|bar3)", isRegex: false },
+      result: { name: "foo", values: ["bar1|bar2|bar3)"] },
+    },
+    {
+      matcher: { name: "foo", value: "(bar1|bar2|bar3", isRegex: false },
+      result: { name: "foo", values: ["(bar1|bar2|bar3"] },
+    },
+    {
+      matcher: { name: "foo", value: "bar1|bar2|bar3", isRegex: true },
+      result: { name: "foo", values: ["bar1", "bar2", "bar3"] },
+    },
+    {
+      matcher: { name: "foo", value: "bar1|bar2|bar3", isRegex: false },
+      result: { name: "foo", values: ["bar1|bar2|bar3"] },
+    },
+    {
+      matcher: { name: "foo", value: "(.+|bar2|bar3)", isRegex: true },
+      result: { name: "foo", values: ["(.+|bar2|bar3)"] },
+    },
+    {
+      matcher: { name: "foo", value: "bar1|bar?|bar3)", isRegex: true },
+      result: { name: "foo", values: ["bar1|bar?|bar3)"] },
+    },
+    {
+      matcher: { name: "foo", value: "server(0|1)", isRegex: true },
+      result: { name: "foo", values: ["server(0|1)"] },
+    },
+  ];
+  for (const t of tests) {
+    it(`fillFormFromSilence() unpacks ${t.matcher.name}=${t.matcher.value} isRegex=${t.matcher.isRegex} into ${t.result.name}=${t.result.values}`, () => {
+      const silenceFormStorestore = new SilenceFormStore();
+      const alertmanager = MockAlertmanager();
+      const silence = MockSilence();
+      silence.matchers = [t.matcher];
+      silenceFormStorestore.data.fillFormFromSilence(alertmanager, silence);
+
+      expect(silenceFormStorestore.data.matchers).toHaveLength(1);
+      expect(silenceFormStorestore.data.matchers).toContainEqual(
+        expect.objectContaining({
+          name: t.result.name,
+          values: t.result.values.map((v) => ({ label: v, value: v })),
+          isRegex: t.matcher.isRegex,
+        })
+      );
+    });
+  }
+
   it("toAlertmanagerPayload constains id when store.data.silenceID is set", () => {
     store.data.silenceID = "12345";
     expect(store.data.toAlertmanagerPayload).toMatchObject({