diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9988bca9..20cdebe4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,12 @@ This project uses semantic versioning for public releases. Use `MAJOR.MINOR.PATC
 - `MINOR` changes add user-visible features and improvements.
 - `PATCH` changes fix bugs, polish existing behavior, or make small internal improvements.
 
+## [Unreleased]
+
+### Fixed
+
+- Fixed the configured transcription, post-processing, and context timeouts being silently capped at 30 seconds by a session-level resource timeout, which broke long transfers to slow local models.
+
 ## [1.1.0] - 2026-06-03
 
 ### Added
diff --git a/Sources/LLMAPITransport.swift b/Sources/LLMAPITransport.swift
index e414d13b..698010c9 100644
--- a/Sources/LLMAPITransport.swift
+++ b/Sources/LLMAPITransport.swift
@@ -1,23 +1,49 @@
 import Foundation
 
 enum LLMAPITransport {
-    private static let requestSession: URLSession = {
-        makeEphemeralSession()
-    }()
+    /// Floor for the whole-transfer budget so requests that never set an
+    /// explicit timeout still fail within a reasonable window.
+    private static let minimumResourceTimeout: TimeInterval = 30
 
-    private static func makeEphemeralSession() -> URLSession {
+    /// Reusable sessions keyed by resource timeout, so connection reuse is
+    /// preserved while each request still gets a whole-transfer budget that
+    /// honors the caller's configured timeout. Only a handful of distinct
+    /// timeout values ever exist (one per timeout setting).
+    private static var sessionsByResourceTimeout: [TimeInterval: URLSession] = [:]
+    private static let sessionsLock = NSLock()
+
+    private static func makeEphemeralSession(resourceTimeout: TimeInterval) -> URLSession {
         let configuration = URLSessionConfiguration.ephemeral
         configuration.requestCachePolicy = .reloadIgnoringLocalCacheData
         configuration.urlCache = nil
         configuration.timeoutIntervalForRequest = 20
-        configuration.timeoutIntervalForResource = 30
+        configuration.timeoutIntervalForResource = resourceTimeout
         return URLSession(configuration: configuration)
     }
 
+    /// timeoutIntervalForResource caps the entire transfer and has no
+    /// per-request override, so derive it from the caller's configured
+    /// timeout (e.g. post_processing_timeout_seconds) instead of a fixed cap.
+    private static func resourceTimeout(for request: URLRequest) -> TimeInterval {
+        max(request.timeoutInterval, minimumResourceTimeout)
+    }
+
+    private static func sharedSession(for request: URLRequest) -> URLSession {
+        let timeout = resourceTimeout(for: request)
+        sessionsLock.lock()
+        defer { sessionsLock.unlock() }
+        if let existing = sessionsByResourceTimeout[timeout] {
+            return existing
+        }
+        let session = makeEphemeralSession(resourceTimeout: timeout)
+        sessionsByResourceTimeout[timeout] = session
+        return session
+    }
+
     static func data(
         for request: URLRequest
     ) async throws -> (Data, URLResponse) {
-        try await requestSession.data(for: request)
+        try await sharedSession(for: request).data(for: request)
     }
 
     static func upload(
@@ -26,7 +52,7 @@ enum LLMAPITransport {
     ) async throws -> (Data, URLResponse) {
         // Use a fresh session for each upload so a bad reused connection cannot
         // poison subsequent transcription uploads.
-        let session = makeEphemeralSession()
+        let session = makeEphemeralSession(resourceTimeout: resourceTimeout(for: request))
         defer { session.finishTasksAndInvalidate() }
         return try await session.upload(for: request, from: bodyData)
     }