diff --git a/site/src/components/AppLink/AppLink.stories.tsx b/site/src/components/AppLink/AppLink.stories.tsx
index 0df7ac73a7..47f89bfb9d 100644
--- a/site/src/components/AppLink/AppLink.stories.tsx
+++ b/site/src/components/AppLink/AppLink.stories.tsx
@@ -29,8 +29,8 @@ const Template: Story<AppLinkProps> = (args) => (
       clearProxy: () => {
         return
       },
-      refetchProxyLatencies: () => {
-        return
+      refetchProxyLatencies: (): Date => {
+        return new Date()
       },
     }}
   >
diff --git a/site/src/components/Navbar/NavbarView.tsx b/site/src/components/Navbar/NavbarView.tsx
index 618ad7d6cc..2f78fd47cb 100644
--- a/site/src/components/Navbar/NavbarView.tsx
+++ b/site/src/components/Navbar/NavbarView.tsx
@@ -188,6 +188,7 @@ const ProxyMenu: FC<{ proxyContextValue: ProxyContextValue }> = ({
 }) => {
   const buttonRef = useRef<HTMLButtonElement>(null)
   const [isOpen, setIsOpen] = useState(false)
+  const [refetchDate, setRefetchDate] = useState<Date>()
   const selectedProxy = proxyContextValue.proxy.proxy
   const refreshLatencies = proxyContextValue.refetchProxyLatencies
   const closeMenu = () => setIsOpen(false)
@@ -196,6 +197,26 @@ const ProxyMenu: FC<{ proxyContextValue: ProxyContextValue }> = ({
   const isLoadingLatencies = Object.keys(latencies).length === 0
   const isLoading = proxyContextValue.isLoading || isLoadingLatencies
   const permissions = usePermissions()
+  const proxyLatencyLoading = (proxy: TypesGen.Region): boolean => {
+    if (!refetchDate) {
+      // Only show loading if the user manually requested a refetch
+      return false
+    }
+
+    const latency = latencies?.[proxy.id]
+    // Only show a loading spinner if:
+    //  - A latency exists. This means the latency was fetched at some point, so the
+    //    loader *should* be resolved.
+    //  - The proxy is healthy. If it is not, the loader might never resolve.
+    //  - The latency reported is older than the refetch date. This means the latency
+    //    is stale and we should show a loading spinner until the new latency is
+    //    fetched.
+    if (proxy.healthy && latency && latency.at < refetchDate) {
+      return true
+    }
+
+    return false
+  }
 
   if (isLoading) {
     return (
@@ -234,6 +255,7 @@ const ProxyMenu: FC<{ proxyContextValue: ProxyContextValue }> = ({
             {selectedProxy.display_name}
             <ProxyStatusLatency
               latency={latencies?.[selectedProxy.id]?.latencyMS}
+              isLoading={proxyLatencyLoading(selectedProxy)}
             />
           </Box>
         ) : (
@@ -277,7 +299,10 @@ const ProxyMenu: FC<{ proxyContextValue: ProxyContextValue }> = ({
                 />
               </Box>
               {proxy.display_name}
-              <ProxyStatusLatency latency={latencies?.[proxy.id]?.latencyMS} />
+              <ProxyStatusLatency
+                latency={latencies?.[proxy.id]?.latencyMS}
+                isLoading={proxyLatencyLoading(proxy)}
+              />
             </Box>
           </MenuItem>
         ))}
@@ -298,7 +323,8 @@ const ProxyMenu: FC<{ proxyContextValue: ProxyContextValue }> = ({
             // Stop the menu from closing
             e.stopPropagation()
             // Refresh the latencies.
-            refreshLatencies()
+            const refetchDate = refreshLatencies()
+            setRefetchDate(refetchDate)
           }}
         >
           Refresh Latencies
diff --git a/site/src/components/ProxyStatusLatency/ProxyStatusLatency.tsx b/site/src/components/ProxyStatusLatency/ProxyStatusLatency.tsx
index 6988050e55..301efe990c 100644
--- a/site/src/components/ProxyStatusLatency/ProxyStatusLatency.tsx
+++ b/site/src/components/ProxyStatusLatency/ProxyStatusLatency.tsx
@@ -4,11 +4,29 @@ import Box from "@mui/material/Box"
 import Tooltip from "@mui/material/Tooltip"
 import { FC } from "react"
 import { getLatencyColor } from "utils/latency"
+import CircularProgress from "@mui/material/CircularProgress"
 
-export const ProxyStatusLatency: FC<{ latency?: number }> = ({ latency }) => {
+export const ProxyStatusLatency: FC<{
+  latency?: number
+  isLoading?: boolean
+}> = ({ latency, isLoading }) => {
   const theme = useTheme()
   const color = getLatencyColor(theme, latency)
 
+  if (isLoading) {
+    return (
+      <Tooltip title="Loading latency...">
+        <CircularProgress
+          size="14px"
+          sx={{
+            // Always use the no latency color for loading.
+            color: getLatencyColor(theme, undefined),
+          }}
+        />
+      </Tooltip>
+    )
+  }
+
   if (!latency) {
     return (
       <Tooltip title="Latency not available">
diff --git a/site/src/components/Resources/AgentRow.stories.tsx b/site/src/components/Resources/AgentRow.stories.tsx
index 7ffef16e04..522fe37cb0 100644
--- a/site/src/components/Resources/AgentRow.stories.tsx
+++ b/site/src/components/Resources/AgentRow.stories.tsx
@@ -68,8 +68,8 @@ const TemplateFC = (
         clearProxy: () => {
           return
         },
-        refetchProxyLatencies: () => {
-          return
+        refetchProxyLatencies: (): Date => {
+          return new Date()
         },
       }}
     >
diff --git a/site/src/components/Resources/ResourceCard.stories.tsx b/site/src/components/Resources/ResourceCard.stories.tsx
index 8de2c49b1e..4b8a33c90e 100644
--- a/site/src/components/Resources/ResourceCard.stories.tsx
+++ b/site/src/components/Resources/ResourceCard.stories.tsx
@@ -33,8 +33,8 @@ Example.args = {
         clearProxy: () => {
           return
         },
-        refetchProxyLatencies: () => {
-          return
+        refetchProxyLatencies: (): Date => {
+          return new Date()
         },
       }}
     >
@@ -106,8 +106,8 @@ BunchOfMetadata.args = {
         clearProxy: () => {
           return
         },
-        refetchProxyLatencies: () => {
-          return
+        refetchProxyLatencies: (): Date => {
+          return new Date()
         },
       }}
     >
diff --git a/site/src/components/Workspace/Workspace.stories.tsx b/site/src/components/Workspace/Workspace.stories.tsx
index 2b2df5e5f6..70b022f1ec 100644
--- a/site/src/components/Workspace/Workspace.stories.tsx
+++ b/site/src/components/Workspace/Workspace.stories.tsx
@@ -42,8 +42,8 @@ const meta: Meta<typeof Workspace> = {
             setProxy: () => {
               return
             },
-            refetchProxyLatencies: () => {
-              return
+            refetchProxyLatencies: (): Date => {
+              return new Date()
             },
           }}
         >
diff --git a/site/src/contexts/ProxyContext.tsx b/site/src/contexts/ProxyContext.tsx
index 82d83506dd..913b605f48 100644
--- a/site/src/contexts/ProxyContext.tsx
+++ b/site/src/contexts/ProxyContext.tsx
@@ -53,7 +53,7 @@ export interface ProxyContextValue {
   proxyLatencies: Record<string, ProxyLatencyReport>
   // refetchProxyLatencies will trigger refreshing of the proxy latencies. By default the latencies
   // are loaded once.
-  refetchProxyLatencies: () => void
+  refetchProxyLatencies: () => Date
   // setProxy is a function that sets the user's selected proxy. This function should
   // only be called if the user is manually selecting a proxy. This value is stored in local
   // storage and will persist across reloads and tabs.