feat: prompt for API key when server requires authentication

apps/reasondb-client/src/App.tsx

@@ -34,12 +34,24 @@ function App() {
       useSsl: activeConnection.ssl,
     })
 
-    client.testConnection().then((result) => {
-      if (result.success) {
-        setClient(activeConnectionId, client)
-      } else {
+    client.testConnection().then(async (result) => {
+      if (!result.success) {
         setActiveConnection(null)
+        return
+      }
+
+      // If the persisted connection has no API key, check whether auth is required.
+      // If so, drop the active connection so the user is brought back to the
+      // connection list where clicking the row will show the API key prompt.
+      if (!activeConnection.apiKey) {
+        const { authRequired } = await client.checkAuth()
+        if (authRequired) {
+          setActiveConnection(null)
+          return
+        }
       }
+
+      setClient(activeConnectionId, client)
     }).catch(() => {
       setActiveConnection(null)
     })

apps/reasondb-client/src/components/connection/ApiKeyPromptDialog.tsx

@@ -0,0 +1,111 @@
+import { useState, useEffect } from 'react'
+import {
+  Dialog,
+  DialogContent,
+  DialogHeader,
+  DialogTitle,
+  DialogDescription,
+  DialogFooter,
+} from '@/components/ui/Dialog'
+import { Input } from '@/components/ui/Input'
+import { Button } from '@/components/ui/Button'
+import { Label } from '@/components/ui/Label'
+import { Key, CircleNotch, WarningCircle } from '@phosphor-icons/react'
+
+interface ApiKeyPromptDialogProps {
+  open: boolean
+  connectionName: string
+  /** Called with the submitted key; return false to show a validation error */
+  onSubmit: (apiKey: string) => Promise<boolean>
+  onCancel: () => void
+}
+
+export function ApiKeyPromptDialog({
+  open,
+  connectionName,
+  onSubmit,
+  onCancel,
+}: ApiKeyPromptDialogProps) {
+  const [apiKey, setApiKey] = useState('')
+  const [loading, setLoading] = useState(false)
+  const [error, setError] = useState<string | null>(null)
+
+  // Reset state when dialog opens
+  useEffect(() => {
+    if (open) {
+      setApiKey('')
+      setError(null)
+      setLoading(false)
+    }
+  }, [open])
+
+  const handleSubmit = async (e: React.FormEvent) => {
+    e.preventDefault()
+    if (!apiKey.trim()) {
+      setError('API key is required')
+      return
+    }
+
+    setLoading(true)
+    setError(null)
+
+    try {
+      const ok = await onSubmit(apiKey.trim())
+      if (!ok) {
+        setError('Invalid API key — authentication failed')
+      }
+    } catch {
+      setError('Connection error — please check the key and try again')
+    } finally {
+      setLoading(false)
+    }
+  }
+
+  return (
+    <Dialog open={open} onOpenChange={(v) => { if (!v) onCancel() }}>
+      <DialogContent className="sm:max-w-md">
+        <DialogHeader>
+          <DialogTitle className="flex items-center gap-2">
+            <Key size={18} weight="duotone" className="text-blue" />
+            Authentication Required
+          </DialogTitle>
+          <DialogDescription>
+            <strong>{connectionName}</strong> requires an API key. Enter your key to connect.
+          </DialogDescription>
+        </DialogHeader>
+
+        <form onSubmit={handleSubmit} className="space-y-4 py-2">
+          <div className="space-y-1.5">
+            <Label htmlFor="api-key-input">API Key</Label>
+            <Input
+              id="api-key-input"
+              type="password"
+              placeholder="Enter your API key…"
+              value={apiKey}
+              onChange={(e) => setApiKey(e.target.value)}
+              autoFocus
+              disabled={loading}
+            />
+          </div>
+
+          {error && (
+            <div className="flex items-center gap-2 text-sm text-red rounded-md bg-red/10 px-3 py-2">
+              <WarningCircle size={16} weight="fill" className="shrink-0" />
+              <span>{error}</span>
+            </div>
+          )}
+
+          <DialogFooter>
+            <Button type="button" variant="ghost" onClick={onCancel} disabled={loading}>
+              Cancel
+            </Button>
+            <Button type="submit" disabled={loading || !apiKey.trim()}>
+              {loading && <CircleNotch size={14} className="mr-1.5 animate-spin" />}
+              Connect
+            </Button>
+          </DialogFooter>
+        </form>
+      </DialogContent>
+    </Dialog>
+  )
+}

apps/reasondb-client/src/components/layout/Sidebar.tsx

@@ -1,4 +1,4 @@
-import { useState } from 'react'
+import { useState, useRef } from 'react'
 import {
   Clock,
   Star,
@@ -17,8 +17,9 @@ import { useLlmHealthStore } from '@/stores/llmHealthStore'
 import { useQueryStore } from '@/stores/queryStore'
 import { ConnectionList } from '@/components/connection/ConnectionList'
 import { ConnectionForm } from '@/components/connection/ConnectionForm'
+import { ApiKeyPromptDialog } from '@/components/connection/ApiKeyPromptDialog'
 import { TableBrowser } from '@/components/table/TableBrowser'
-import { createClient, setClient, removeClient } from '@/lib/api'
+import { createClient, setClient, removeClient, type ReasonDBClient } from '@/lib/api'
 
 export function Sidebar() {
   const { 
@@ -31,6 +32,10 @@ export function Sidebar() {
   const { history, savedQueries } = useQueryStore()
   const [editingConnection, setEditingConnection] = useState<Connection | undefined>()
 
+  // Pending auth — set when a server requires auth but the connection has no key
+  const [pendingAuthConnection, setPendingAuthConnection] = useState<Connection | null>(null)
+  const pendingClientRef = useRef<ReasonDBClient | null>(null)
+
   const handleConnect = async (connection: Connection) => {
     setConnecting(true)
     setConnectionError(null)
@@ -44,20 +49,60 @@ export function Sidebar() {
       })
 
       const result = await client.testConnection()
-
-      if (result.success) {
-        setClient(connection.id, client)
-        setActiveConnection(connection.id)
-      } else {
+
+      if (!result.success) {
         setConnectionError(result.error || 'Connection failed')
+        return
+      }
+
+      // If no apiKey is already configured, probe to see if the server requires one
+      if (!connection.apiKey) {
+        const { authRequired } = await client.checkAuth()
+        if (authRequired) {
+          // Park the client and surface the API key prompt
+          pendingClientRef.current = client
+          setPendingAuthConnection(connection)
+          return
+        }
       }
+
+      setClient(connection.id, client)
+      setActiveConnection(connection.id)
     } catch (error) {
       setConnectionError(error instanceof Error ? error.message : 'Connection failed')
     } finally {
       setConnecting(false)
     }
   }
 
+  const handleApiKeySubmit = async (apiKey: string): Promise<boolean> => {
+    if (!pendingAuthConnection || !pendingClientRef.current) return false
+
+    const client = pendingClientRef.current
+    client.updateApiKey(apiKey)
+
+    // Validate the key by making a real authenticated request
+    try {
+      await client.listTables()
+    } catch {
+      // 401/403 or other error — key is invalid or request failed
+      return false
+    }
+
+    // Key is valid — complete the connection
+    setClient(pendingAuthConnection.id, client)
+    setActiveConnection(pendingAuthConnection.id)
+    setPendingAuthConnection(null)
+    pendingClientRef.current = null
+    return true
+  }
+
+  const handleApiKeyCancel = () => {
+    setPendingAuthConnection(null)
+    pendingClientRef.current = null
+    setConnecting(false)
+  }
+
   const handleDisconnect = () => {
     if (activeConnectionId) {
       removeClient(activeConnectionId)
@@ -218,6 +263,13 @@ export function Sidebar() {
         onOpenChange={setShowConnectionForm}
         editConnection={editingConnection}
       />
+
+      <ApiKeyPromptDialog
+        open={pendingAuthConnection !== null}
+        connectionName={pendingAuthConnection?.name ?? ''}
+        onSubmit={handleApiKeySubmit}
+        onCancel={handleApiKeyCancel}
+      />
     </nav>
   )
 }

apps/reasondb-client/src/lib/api.ts

@@ -770,6 +770,38 @@ class ReasonDBClient {
     requestCache.clear()
   }
 
+  // ==================== Auth ====================
+
+  /**
+   * Update the API key on this client instance (in-memory only).
+   * Called after a successful auth prompt so the client can make authenticated requests.
+   */
+  updateApiKey(apiKey: string): void {
+    this.apiKey = apiKey
+  }
+
+  /**
+   * Detect whether the server requires an API key by probing /v1/tables
+   * without any auth header.
+   *
+   * Returns `{ authRequired: true }` on 401/403, `{ authRequired: false }` on
+   * any successful response, and `{ authRequired: false, error }` on network
+   * errors so callers don't block the connect flow for transient failures.
+   */
+  async checkAuth(): Promise<{ authRequired: boolean; error?: string }> {
+    const url = `${this.baseUrl}/v1/tables`
+    try {
+      const response = await fetch(url, { method: 'GET' })
+      if (response.status === 401 || response.status === 403) {
+        return { authRequired: true }
+      }
+      return { authRequired: false }
+    } catch {
+      // Network error — treat as no auth required so we don't block the flow
+      return { authRequired: false }
+    }
+  }
+
   // ==================== Health ====================
 
   /**