diff --git a/VoiceInk/Services/AIEnhancementService.swift b/VoiceInk/Services/AIEnhancementService.swift
index 663ef34..7ae13d8 100644
--- a/VoiceInk/Services/AIEnhancementService.swift
+++ b/VoiceInk/Services/AIEnhancementService.swift
@@ -261,6 +261,8 @@ class AIEnhancementService: ObservableObject {
                     
                     let filteredText = AIEnhancementOutputFilter.filter(enhancedText.trimmingCharacters(in: .whitespacesAndNewlines))
                     return filteredText
+                } else if (500...599).contains(httpResponse.statusCode) {
+                    throw EnhancementError.serverError
                 } else {
                     let errorString = String(data: data, encoding: .utf8) ?? "Could not decode error response."
                     throw EnhancementError.customError("HTTP \(httpResponse.statusCode): \(errorString)")
@@ -268,6 +270,8 @@ class AIEnhancementService: ObservableObject {
                 
             } catch let error as EnhancementError {
                 throw error
+            } catch let error as URLError {
+                throw error
             } catch {
                 throw EnhancementError.customError(error.localizedDescription)
             }
@@ -312,6 +316,8 @@ class AIEnhancementService: ObservableObject {
 
                     let filteredText = AIEnhancementOutputFilter.filter(enhancedText.trimmingCharacters(in: .whitespacesAndNewlines))
                     return filteredText
+                } else if (500...599).contains(httpResponse.statusCode) {
+                    throw EnhancementError.serverError
                 } else {
                     let errorString = String(data: data, encoding: .utf8) ?? "Could not decode error response."
                     throw EnhancementError.customError("HTTP \(httpResponse.statusCode): \(errorString)")
@@ -319,19 +325,66 @@ class AIEnhancementService: ObservableObject {
 
             } catch let error as EnhancementError {
                 throw error
+            } catch let error as URLError {
+                throw error
             } catch {
                 throw EnhancementError.customError(error.localizedDescription)
             }
         }
     }
     
+    private func makeRequestWithRetry(text: String, mode: EnhancementPrompt, maxRetries: Int = 3, initialDelay: TimeInterval = 1.0) async throws -> String {
+        var retries = 0
+        var currentDelay = initialDelay
+
+        while retries < maxRetries {
+            do {
+                return try await makeRequest(text: text, mode: mode)
+            } catch let error as EnhancementError {
+                switch error {
+                case .networkError, .serverError:
+                    retries += 1
+                    if retries < maxRetries {
+                        logger.warning("Request failed, retrying in \(currentDelay)s... (Attempt \(retries)/\(maxRetries))")
+                        try await Task.sleep(nanoseconds: UInt64(currentDelay * 1_000_000_000))
+                        currentDelay *= 2 // Exponential backoff
+                    } else {
+                        logger.error("Request failed after \(maxRetries) retries.")
+                        throw error
+                    }
+                default:
+                    throw error
+                }
+            } catch {
+                // For other errors, check if it's a network-related URLError
+                let nsError = error as NSError
+                if nsError.domain == NSURLErrorDomain && [NSURLErrorNotConnectedToInternet, NSURLErrorTimedOut, NSURLErrorNetworkConnectionLost].contains(nsError.code) {
+                    retries += 1
+                    if retries < maxRetries {
+                        logger.warning("Request failed with network error, retrying in \(currentDelay)s... (Attempt \(retries)/\(maxRetries))")
+                        try await Task.sleep(nanoseconds: UInt64(currentDelay * 1_000_000_000))
+                        currentDelay *= 2 // Exponential backoff
+                    } else {
+                        logger.error("Request failed after \(maxRetries) retries with network error.")
+                        throw EnhancementError.networkError
+                    }
+                } else {
+                    throw error
+                }
+            }
+        }
+
+        // This part should ideally not be reached, but as a fallback:
+        throw EnhancementError.enhancementFailed
+    }
+
     func enhance(_ text: String) async throws -> (String, TimeInterval, String?) {
         let startTime = Date()
         let enhancementPrompt: EnhancementPrompt = .transcriptionEnhancement
         let promptName = activePrompt?.title
         
         do {
-            let result = try await makeRequest(text: text, mode: enhancementPrompt)
+            let result = try await makeRequestWithRetry(text: text, mode: enhancementPrompt)
             let endTime = Date()
             let duration = endTime.timeIntervalSince(startTime)
             return (result, duration, promptName)
@@ -404,6 +457,7 @@ enum EnhancementError: Error {
     case invalidResponse
     case enhancementFailed
     case networkError
+    case serverError
     case customError(String)
 }
 
@@ -418,6 +472,8 @@ extension EnhancementError: LocalizedError {
             return "AI enhancement failed to process the text."
         case .networkError:
             return "Network connection failed. Check your internet."
+        case .serverError:
+            return "The AI provider's server encountered an error. Please try again later."
         case .customError(let message):
             return message
         }