diff --git a/.changeset/rare-items-arrive.md b/.changeset/rare-items-arrive.md
new file mode 100644
index 00000000000..8e0583a9d55
--- /dev/null
+++ b/.changeset/rare-items-arrive.md
@@ -0,0 +1,5 @@
+---
+"@atproto/pds": patch
+---
+
+Use a less cryptic error message when proxying fails
diff --git a/.changeset/thirty-masks-watch.md b/.changeset/thirty-masks-watch.md
new file mode 100644
index 00000000000..b8c486986d3
--- /dev/null
+++ b/.changeset/thirty-masks-watch.md
@@ -0,0 +1,5 @@
+---
+"@atproto/pds": patch
+---
+
+Allow retrying proxied requests
diff --git a/packages/pds/src/config/config.ts b/packages/pds/src/config/config.ts
index 2d901f58ec6..263d987577e 100644
--- a/packages/pds/src/config/config.ts
+++ b/packages/pds/src/config/config.ts
@@ -246,6 +246,10 @@ export const envToCfg = (env: ServerEnvironment): ServerConfig => {
     headersTimeout: env.proxyHeadersTimeout ?? 10e3,
     bodyTimeout: env.proxyBodyTimeout ?? 30e3,
     maxResponseSize: env.proxyMaxResponseSize ?? 10 * 1024 * 1024, // 10mb
+    maxRetries:
+      env.proxyMaxRetries != null && env.proxyMaxRetries > 0
+        ? env.proxyMaxRetries
+        : 0,
     preferCompressed: env.proxyPreferCompressed ?? false,
   }
 
@@ -414,6 +418,7 @@ export type ProxyConfig = {
   headersTimeout: number
   bodyTimeout: number
   maxResponseSize: number
+  maxRetries: number
 
   /**
    * When proxying requests that might get intercepted (for read-after-write) we
diff --git a/packages/pds/src/config/env.ts b/packages/pds/src/config/env.ts
index 0c44e1fdc8d..1d26d4c06a6 100644
--- a/packages/pds/src/config/env.ts
+++ b/packages/pds/src/config/env.ts
@@ -128,6 +128,7 @@ export const readEnv = (): ServerEnvironment => {
     proxyHeadersTimeout: envInt('PDS_PROXY_HEADERS_TIMEOUT'),
     proxyBodyTimeout: envInt('PDS_PROXY_BODY_TIMEOUT'),
     proxyMaxResponseSize: envInt('PDS_PROXY_MAX_RESPONSE_SIZE'),
+    proxyMaxRetries: envInt('PDS_PROXY_MAX_RETRIES'),
     proxyPreferCompressed: envBool('PDS_PROXY_PREFER_COMPRESSED'),
   }
 }
@@ -254,5 +255,6 @@ export type ServerEnvironment = {
   proxyHeadersTimeout?: number
   proxyBodyTimeout?: number
   proxyMaxResponseSize?: number
+  proxyMaxRetries?: number
   proxyPreferCompressed?: boolean
 }
diff --git a/packages/pds/src/context.ts b/packages/pds/src/context.ts
index 49f55ed6bd5..633a48b46dc 100644
--- a/packages/pds/src/context.ts
+++ b/packages/pds/src/context.ts
@@ -63,7 +63,7 @@ export type AppContextOptions = {
   moderationAgent?: AtpAgent
   reportingAgent?: AtpAgent
   entrywayAgent?: AtpAgent
-  proxyAgent: undici.Agent
+  proxyAgent: undici.Dispatcher
   safeFetch: Fetch
   authProvider?: PdsOAuthProvider
   authVerifier: AuthVerifier
@@ -90,7 +90,7 @@ export class AppContext {
   public moderationAgent: AtpAgent | undefined
   public reportingAgent: AtpAgent | undefined
   public entrywayAgent: AtpAgent | undefined
-  public proxyAgent: undici.Agent
+  public proxyAgent: undici.Dispatcher
   public safeFetch: Fetch
   public authVerifier: AuthVerifier
   public authProvider?: PdsOAuthProvider
@@ -264,7 +264,7 @@ export class AppContext {
     })
 
     // An agent for performing HTTP requests based on user provided URLs.
-    const proxyAgent = new undici.Agent({
+    const proxyAgentBase = new undici.Agent({
       allowH2: cfg.proxy.allowHTTP2, // This is experimental
       headersTimeout: cfg.proxy.headersTimeout,
       maxResponseSize: cfg.proxy.maxResponseSize,
@@ -286,6 +286,14 @@ export class AppContext {
         lookup: cfg.proxy.disableSsrfProtection ? undefined : unicastLookup,
       },
     })
+    const proxyAgent =
+      cfg.proxy.maxRetries > 0
+        ? new undici.RetryAgent(proxyAgentBase, {
+            statusCodes: [], // Only retry on socket errors
+            methods: ['GET', 'HEAD'],
+            maxRetries: cfg.proxy.maxRetries,
+          })
+        : proxyAgentBase
 
     // A fetch() function that protects against SSRF attacks, large responses &
     // known bad domains. This function can safely be used to fetch user
diff --git a/packages/pds/src/pipethrough.ts b/packages/pds/src/pipethrough.ts
index 285320d22c6..b326d5fba8b 100644
--- a/packages/pds/src/pipethrough.ts
+++ b/packages/pds/src/pipethrough.ts
@@ -357,9 +357,9 @@ async function pipethroughRequest(
 
 function handleUpstreamRequestError(
   err: unknown,
-  message = 'pipethrough network error',
+  message = 'Upstream service unreachable',
 ): never {
-  httpLogger.warn({ err }, message)
+  httpLogger.error({ err }, message)
   throw new XRPCServerError(ResponseType.UpstreamFailure, message, undefined, {
     cause: err,
   })
@@ -520,18 +520,11 @@ async function tryParsingError(
   }
 }
 
-export async function bufferUpstreamResponse(
+async function bufferUpstreamResponse(
   readable: Readable,
   contentEncoding?: string | string[],
 ): Promise<Buffer> {
   try {
-    // Needed for type-safety (should never happen irl)
-    if (Array.isArray(contentEncoding)) {
-      throw new TypeError(
-        'upstream service returned multiple content-encoding headers',
-      )
-    }
-
     return await streamToNodeBuffer(decodeStream(readable, contentEncoding))
   } catch (err) {
     if (!readable.destroyed) readable.destroy()
@@ -561,7 +554,11 @@ export async function asPipeThroughBuffer(
 // Response parsing/forwarding
 // -------------------
 
-const RES_HEADERS_TO_FORWARD = ['atproto-repo-rev', 'atproto-content-labelers']
+const RES_HEADERS_TO_FORWARD = [
+  'atproto-repo-rev',
+  'atproto-content-labelers',
+  'retry-after',
+]
 
 function* responseHeaders(
   headers: IncomingHttpHeaders,
@@ -584,7 +581,11 @@ function* responseHeaders(
   for (let i = 0; i < RES_HEADERS_TO_FORWARD.length; i++) {
     const name = RES_HEADERS_TO_FORWARD[i]
     const val = headers[name]
-    if (typeof val === 'string') yield [name, val]
+
+    if (val != null) {
+      const value: string = Array.isArray(val) ? val.join(',') : val
+      yield [name, value]
+    }
   }
 }
 
diff --git a/packages/pds/tests/proxied/proxy-catchall.test.ts b/packages/pds/tests/proxied/proxy-catchall.test.ts
index e6726d79813..7ed68d1ae30 100644
--- a/packages/pds/tests/proxied/proxy-catchall.test.ts
+++ b/packages/pds/tests/proxied/proxy-catchall.test.ts
@@ -116,7 +116,7 @@ describe('proxy header', () => {
     for (const lex of lexicons) client.lex.add(lex)
 
     await expect(client.call('com.example.ok')).rejects.toThrow(
-      'pipethrough network error',
+      'Upstream service unreachable',
     )
   })