diff --git a/frontend/src/lib/components/VersionChecker/versionCheckerLogic.test.ts b/frontend/src/lib/components/VersionChecker/versionCheckerLogic.test.ts
index 52cfe0740f596..22431153935d2 100644
--- a/frontend/src/lib/components/VersionChecker/versionCheckerLogic.test.ts
+++ b/frontend/src/lib/components/VersionChecker/versionCheckerLogic.test.ts
@@ -105,4 +105,46 @@ describe('versionCheckerLogic', () => {
         await expectLogic(logic).toFinishAllListeners()
         expectLogic(logic).toMatchValues({ versionWarning: options.expectation })
     })
+
+    it.each([
+        {
+            usedVersions: [
+                { version: '1.9.0', timestamp: '2023-01-01T12:00:00Z' },
+                { version: '1.83.1', timestamp: '2023-01-01T10:00:00Z' },
+            ],
+            expectation: {
+                currentVersion: '1.83.1',
+                latestVersion: '1.84.0',
+                diff: 1,
+                level: 'info',
+            },
+        },
+        {
+            usedVersions: [
+                { version: '1.80.0', timestamp: '2023-01-01T12:00:00Z' },
+                { version: '1.83.1', timestamp: '2023-01-01T10:00:00Z' },
+                { version: '1.20.1', timestamp: '2023-01-01T10:00:00Z' },
+                { version: '1.0.890', timestamp: '2023-01-01T10:00:00Z' },
+                { version: '0.89.5', timestamp: '2023-01-01T10:00:00Z' },
+                { version: '0.0.5', timestamp: '2023-01-01T10:00:00Z' },
+                { version: '1.84.0', timestamp: '2023-01-01T08:00:00Z' },
+            ],
+            expectation: null,
+        },
+        {
+            usedVersions: [
+                { version: '1.80.0', timestamp: '2023-01-01T12:00:00Z' },
+                { version: '1.83.1-beta', timestamp: '2023-01-01T10:00:00Z' },
+                { version: '1.84.0-delta', timestamp: '2023-01-01T08:00:00Z' },
+            ],
+            expectation: { currentVersion: '1.84.0-delta', diff: 1, latestVersion: '1.84.0', level: 'info' },
+        },
+    ])('when having multiple versions used, should match with the latest one', async (options) => {
+        useMockedVersions([{ version: '1.84.0' }], options.usedVersions)
+
+        logic.mount()
+
+        await expectLogic(logic).toFinishAllListeners()
+        expectLogic(logic).toMatchValues({ versionWarning: options.expectation })
+    })
 })
diff --git a/frontend/src/lib/components/VersionChecker/versionCheckerLogic.ts b/frontend/src/lib/components/VersionChecker/versionCheckerLogic.ts
index e08b5c26da4cf..acc1897bc78f2 100644
--- a/frontend/src/lib/components/VersionChecker/versionCheckerLogic.ts
+++ b/frontend/src/lib/components/VersionChecker/versionCheckerLogic.ts
@@ -88,18 +88,24 @@ export const versionCheckerLogic = kea<versionCheckerLogicType>([
             }
 
             const latestVersion = values.availableVersions[0].version
-            const currentVersion = values.usedVersions[0].version
 
-            if (latestVersion === currentVersion) {
+            // reverse sort, hence reversed arguments to localeCompare.
+            // We want the highest semantic version to be the latest used one, rather than
+            // the one with the latest timestamp, because secondary installations can spew old versions
+            const latestUsedVersion = [...values.usedVersions].sort((a, b) =>
+                b.version.localeCompare(a.version, undefined, { numeric: true })
+            )[0].version
+
+            if (latestVersion === latestUsedVersion) {
                 actions.setVersionWarning(null)
                 return
             }
 
-            let diff = values.availableVersions.findIndex((v) => v.version === currentVersion)
+            let diff = values.availableVersions.findIndex((v) => v.version === latestUsedVersion)
             diff = diff === -1 ? values.availableVersions.length : diff
 
             const warning: SDKVersionWarning = {
-                currentVersion,
+                currentVersion: latestUsedVersion,
                 latestVersion,
                 diff,
                 level: diff > 20 ? 'error' : diff > 10 ? 'warning' : 'info',