@@ -162,6 +162,23 @@ describe('MCP OAuth start route', () => {
     expect(body.error).not.toContain('ECONNREFUSED')
     expect(body.error).not.toContain('internal-db-host')
   })
+
+  it('returns an actionable 4xx when the server does not support dynamic client registration', async () => {
+    mcpOauthMockFns.mockMcpAuthGuarded.mockRejectedValueOnce(
+      new Error('Incompatible auth server: does not support dynamic client registration')
+    )
+    const request = new NextRequest(
+      'http://localhost:3000/api/mcp/oauth/start?workspaceId=workspace-1&serverId=server-1'
+    )
+
+    const response = await GET(request)
+    const body = await response.json()
+
+    expect(response.status).toBe(422)
+    expect(body.error).toBe(
+      "This server doesn't support automatic OAuth client registration. Add a pre-registered OAuth client ID and secret, or configure a token instead."
+    )
+  })
 })
 
 describe('surfaceOauthError', () => {
 
@@ -2,7 +2,7 @@ import { OAuthError, ServerError } from '@modelcontextprotocol/sdk/server/auth/e
 import { db } from '@sim/db'
 import { mcpServers } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
-import { toError } from '@sim/utils/errors'
+import { getErrorMessage, toError } from '@sim/utils/errors'
 import { and, eq, isNull } from 'drizzle-orm'
 import type { NextRequest } from 'next/server'
 import { NextResponse } from 'next/server'
@@ -25,6 +25,14 @@ import { createMcpErrorResponse } from '@/lib/mcp/utils'
 const logger = createLogger('McpOauthStartAPI')
 const OAUTH_START_TTL_MS = 10 * 60 * 1000
 const MAX_SURFACED_ERROR_LENGTH = 250
+const DCR_UNSUPPORTED_MESSAGE =
+  "This server doesn't support automatic OAuth client registration. Add a pre-registered OAuth client ID and secret, or configure a token instead."
+
+function isDynamicClientRegistrationUnsupported(error: unknown): boolean {
+  return getErrorMessage(error, '')
+    .toLowerCase()
+    .includes('does not support dynamic client registration')
+}
 
 export function surfaceOauthError(error: unknown): string {
   // Spec-compliant OAuth servers throw typed subclasses with clean RFC 6749 fields.
@@ -148,6 +156,9 @@ export const GET = withRouteHandler(
             authorizationUrl: e.authorizationUrl,
           })
         }
+        if (isDynamicClientRegistrationUnsupported(e)) {
+          return createMcpErrorResponse(toError(e), DCR_UNSUPPORTED_MESSAGE, 422)
+        }
         throw e
       }
     } catch (error) {
 
@@ -85,7 +85,12 @@ function ServerListItem({
   onViewDetails,
 }: ServerListItemProps) {
   const transportLabel = formatTransportLabel(server.transport || 'http')
-  const toolsLabel = getServerToolsLabel(tools, server.connectionStatus, server.lastError)
+  const toolsLabel = getServerToolsLabel(
+    tools,
+    server.connectionStatus,
+    server.lastError,
+    server.authType
+  )
   const hasConnectionIssue =
     server.connectionStatus === 'error' || server.connectionStatus === 'disconnected'
 
@@ -380,6 +385,8 @@ export function MCP() {
     const refreshAction = getRefreshActionState({
       mutationStatus: isCurrentRefresh ? refreshServerMutation.status : 'idle',
       connectionStatus: isCurrentRefresh ? refreshServerMutation.data?.status : undefined,
+      authType: server.authType,
+      error: isCurrentRefresh ? refreshServerMutation.data?.error : undefined,
       workflowsUpdated: isCurrentRefresh ? refreshServerMutation.data?.workflowsUpdated : undefined,
     })
 
@@ -427,7 +434,12 @@ export function MCP() {
               <div className='flex flex-col gap-2'>
                 <span className='text-[var(--text-muted)] text-caption'>Status</span>
                 <p className='text-[var(--text-error)] text-sm'>
-                  {getServerToolsLabel([], server.connectionStatus, server.lastError)}
+                  {getServerToolsLabel(
+                    [],
+                    server.connectionStatus,
+                    server.lastError,
+                    server.authType
+                  )}
                 </p>
               </div>
             )}
 
@@ -31,6 +31,37 @@ describe('getRefreshActionState', () => {
     })
   })
 
+  it('shows OAuth authorization required when an OAuth refresh finishes disconnected', () => {
+    expect(
+      getRefreshActionState({
+        mutationStatus: 'success',
+        connectionStatus: 'disconnected',
+        authType: 'oauth',
+        workflowsUpdated: 0,
+      })
+    ).toEqual({
+      text: 'OAuth authorization required',
+      textTone: 'error',
+      disabled: false,
+    })
+  })
+
+  it('keeps Failed when a disconnected OAuth refresh has a concrete error', () => {
+    expect(
+      getRefreshActionState({
+        mutationStatus: 'success',
+        connectionStatus: 'disconnected',
+        authType: 'oauth',
+        error: 'The MCP server took too long to respond and timed out',
+        workflowsUpdated: 0,
+      })
+    ).toEqual({
+      text: 'Failed',
+      textTone: 'error',
+      disabled: false,
+    })
+  })
+
   it('preserves successful refresh feedback', () => {
     expect(
       getRefreshActionState({
 
@@ -1,10 +1,12 @@
 import type { MutationStatus } from '@tanstack/react-query'
-import type { RefreshMcpServerResult } from '@/lib/api/contracts/mcp'
+import type { McpServer, RefreshMcpServerResult } from '@/lib/api/contracts/mcp'
 import type { SettingsAction } from '@/app/workspace/[workspaceId]/settings/components/settings-header/settings-header'
 
 interface RefreshActionStateInput {
   mutationStatus: MutationStatus
   connectionStatus?: RefreshMcpServerResult['status']
+  authType?: McpServer['authType']
+  error?: RefreshMcpServerResult['error']
   workflowsUpdated?: number
 }
 
@@ -13,12 +15,23 @@ type RefreshActionState = Pick<SettingsAction, 'text' | 'textTone' | 'disabled'>
 export function getRefreshActionState({
   mutationStatus,
   connectionStatus,
+  authType,
+  error,
   workflowsUpdated,
 }: RefreshActionStateInput): RefreshActionState {
   if (mutationStatus === 'pending') {
     return { text: 'Refreshing...', textTone: undefined, disabled: true }
   }
 
+  if (
+    mutationStatus === 'success' &&
+    connectionStatus === 'disconnected' &&
+    authType === 'oauth' &&
+    !error?.trim()
+  ) {
+    return { text: 'OAuth authorization required', textTone: 'error', disabled: false }
+  }
+
   if (
     mutationStatus === 'error' ||
     (mutationStatus === 'success' && connectionStatus !== 'connected')
 
@@ -12,12 +12,20 @@ describe('getServerToolsLabel', () => {
     expect(getServerToolsLabel([], 'error', null)).toBe('Unable to connect')
   })
 
-  it('shows a disconnected state when OAuth was not completed', () => {
-    expect(getServerToolsLabel([], 'disconnected', null)).toBe('Not Connected')
+  it('shows that OAuth authorization is required when OAuth was not completed', () => {
+    expect(getServerToolsLabel([], 'disconnected', null, 'oauth')).toBe(
+      'OAuth authorization required'
+    )
+  })
+
+  it('keeps the generic disconnected state for non-OAuth servers', () => {
+    expect(getServerToolsLabel([], 'disconnected', null, 'headers')).toBe('Not Connected')
   })
 
   it('shows the persisted error for disconnected connections', () => {
-    expect(getServerToolsLabel([], 'disconnected', 'Request timed out')).toBe('Request timed out')
+    expect(getServerToolsLabel([], 'disconnected', 'Request timed out', 'oauth')).toBe(
+      'Request timed out'
+    )
   })
 
   it('continues showing discovered tools for healthy connections', () => {
 
@@ -7,14 +7,17 @@ interface NamedTool {
 export function getServerToolsLabel(
   tools: NamedTool[],
   connectionStatus?: McpServer['connectionStatus'],
-  lastError?: McpServer['lastError']
+  lastError?: McpServer['lastError'],
+  authType?: McpServer['authType']
 ): string {
   if (connectionStatus === 'error') {
     return lastError?.trim() || 'Unable to connect'
   }
 
   if (connectionStatus === 'disconnected') {
-    return lastError?.trim() || 'Not Connected'
+    return (
+      lastError?.trim() || (authType === 'oauth' ? 'OAuth authorization required' : 'Not Connected')
+    )
   }
 
   const count = tools.length
 
@@ -433,9 +433,34 @@ export function createPinnedLookup(resolvedIP: string): LookupFunction {
  *
  * The `Agent` is captured for the lifetime of the returned function, so repeated
  * calls (e.g. a provider tool loop) reuse its keep-alive connections.
+ *
+ * `allowH2` opts the pinned Agent into HTTP/2 (ALPN-negotiated, h1.1 fallback).
+ * It defaults to `false` to leave existing consumers unchanged. Enabling it does
+ * not weaken pinning: the pinned `connect.lookup` forces every connection on the
+ * Agent to `resolvedIP` regardless of authority, so h2 connection coalescing can
+ * never reach an address other than the validated one.
+ */
+export function createPinnedFetch(
+  resolvedIP: string,
+  options?: { allowH2?: boolean }
+): typeof fetch {
+  return createPinnedFetchWithDispatcher(resolvedIP, options).fetch
+}
+
+/**
+ * Same as {@link createPinnedFetch} but also returns the underlying `Agent` so a
+ * caller with a defined connection lifetime (e.g. a long-lived MCP transport) can
+ * tear the Agent down on close instead of waiting for its idle timeout. Closing
+ * the Agent is what releases any pooled keep-alive / HTTP/2 sockets it holds.
  */
-export function createPinnedFetch(resolvedIP: string): typeof fetch {
-  const dispatcher = new Agent({ connect: { lookup: createPinnedLookup(resolvedIP) } })
+export function createPinnedFetchWithDispatcher(
+  resolvedIP: string,
+  options?: { allowH2?: boolean }
+): { fetch: typeof fetch; dispatcher: Agent } {
+  const dispatcher = new Agent({
+    allowH2: options?.allowH2 ?? false,
+    connect: { lookup: createPinnedLookup(resolvedIP) },
+  })
 
   const pinned = async (input: RequestInfo | URL, init?: RequestInit): Promise<Response> => {
     // double-cast-allowed: DOM RequestInfo/URL and undici fetch input types differ but are structurally compatible at runtime (Node's global fetch IS undici)
@@ -447,7 +472,7 @@ export function createPinnedFetch(resolvedIP: string): typeof fetch {
     return response as unknown as Response
   }
 
-  return pinned
+  return { fetch: pinned, dispatcher }
 }
 
 /**
 
@@ -55,6 +55,18 @@ describe('createPinnedFetch', () => {
     expect(resolved).toEqual({ address: '203.0.113.10', family: 4 })
   })
 
+  it('defaults allowH2 to false so existing consumers are unchanged', () => {
+    createPinnedFetch('203.0.113.10')
+    const opts = capturedAgentOptions[0] as { allowH2?: boolean }
+    expect(opts.allowH2).toBe(false)
+  })
+
+  it('opts the Agent into HTTP/2 when allowH2 is requested', () => {
+    createPinnedFetch('203.0.113.10', { allowH2: true })
+    const opts = capturedAgentOptions[0] as { allowH2?: boolean }
+    expect(opts.allowH2).toBe(true)
+  })
+
   it('uses IPv6 family when the validated IP is IPv6', async () => {
     createPinnedFetch('2606:4700:4700::1111')
     const { connect } = capturedAgentOptions[0] as { connect: { lookup: PinnedLookup } }