diff --git a/Airship/AirshipAutomation/Source/Automation/Engine/AutomationDelayProcessor.swift b/Airship/AirshipAutomation/Source/Automation/Engine/AutomationDelayProcessor.swift
index dc9d09f6b..37f6ebd02 100644
--- a/Airship/AirshipAutomation/Source/Automation/Engine/AutomationDelayProcessor.swift
+++ b/Airship/AirshipAutomation/Source/Automation/Engine/AutomationDelayProcessor.swift
@@ -12,7 +12,7 @@ protocol AutomationDelayProcessorProtocol: Sendable {
     func process(delay: AutomationDelay?, triggerDate: Date) async
 
     // Waits for any delay - 30s and to be a display window if set
-    func preprocess(delay: AutomationDelay?, triggerDate: Date) async
+    func preprocess(delay: AutomationDelay?, triggerDate: Date) async throws
 
     // Checks if conditions are met
     @MainActor
@@ -106,17 +106,19 @@ final class AutomationDelayProcessor: AutomationDelayProcessorProtocol {
         }
     }
 
-    func preprocess(delay: AutomationDelay?, triggerDate: Date) async {
+    func preprocess(delay: AutomationDelay?, triggerDate: Date) async throws {
         guard let delay = delay else { return }
 
         // Handle delay - preprocessSecondsDelayAllowance
         let seconds = remainingSeconds(delay: delay, triggerDate: triggerDate) - Self.preprocessSecondsDelayAllowance
         if seconds > 0 {
-            try? await self.taskSleeper.sleep(timeInterval: seconds)
+            try await self.taskSleeper.sleep(timeInterval: seconds)
         }
 
+        try Task.checkCancellation()
+
         if let window = delay.executionWindow {
-            try? await executionWindowProcessor.process(window: window)
+            try await executionWindowProcessor.process(window: window)
         }
     }
 
diff --git a/Airship/AirshipAutomation/Source/Automation/Engine/AutomationEngine.swift b/Airship/AirshipAutomation/Source/Automation/Engine/AutomationEngine.swift
index 498bee670..e73f30c27 100644
--- a/Airship/AirshipAutomation/Source/Automation/Engine/AutomationEngine.swift
+++ b/Airship/AirshipAutomation/Source/Automation/Engine/AutomationEngine.swift
@@ -26,6 +26,7 @@ actor AutomationEngine : AutomationEngineProtocol {
 
     private var processPendingExecutionTask: Task<Void, Never>?
     private var pendingExecution: [String: PreparedData] = [:]
+    private var preprocessDelayTasks: Set<Task<Bool, Error>> = Set()
 
 
     init(
@@ -143,6 +144,7 @@ actor AutomationEngine : AutomationEngineProtocol {
         }
 
         await self.triggersProcessor.updateSchedules(updated)
+        self.cancelPreprocessDelayTasks()
     }
 
     func cancelSchedules(identifiers: [String]) async throws {
@@ -356,6 +358,32 @@ fileprivate extension AutomationEngine {
         }
     }
 
+    private func preprocessDelay(data: AutomationScheduleData) async -> Bool {
+        guard let delay = data.schedule.delay else { return true }
+        let scheduleID = data.schedule.identifier
+        let triggerDate = data.triggerInfo?.date ?? data.scheduleStateChangeDate
+
+        let task = Task {
+            AirshipLogger.trace("Preprocessing delay \(scheduleID)")
+            try await self.delayProcessor.preprocess(
+                delay: delay,
+                triggerDate: triggerDate
+            )
+            AirshipLogger.trace("Finished preprocessing delay \(scheduleID)")
+            return true
+        }
+
+        preprocessDelayTasks.insert(task)
+        let result = try? await task.value
+        preprocessDelayTasks.remove(task)
+        return result ?? false
+    }
+
+    private func cancelPreprocessDelayTasks() {
+        preprocessDelayTasks.forEach { $0.cancel() }
+        preprocessDelayTasks.removeAll()
+    }
+
     private func processTriggeredSchedule(scheduleID: String) async throws {
         guard
             let data = try await self.store.getSchedule(scheduleID: scheduleID)
@@ -371,12 +399,14 @@ fileprivate extension AutomationEngine {
             return
         }
 
-        AirshipLogger.trace("Preprocessing delay \(scheduleID)")
-        await self.delayProcessor.preprocess(
-            delay: data.schedule.delay,
-            triggerDate: data.triggerInfo?.date ?? data.scheduleStateChangeDate
-        )
-        AirshipLogger.trace("Finished preprocessing delay \(scheduleID)")
+        guard 
+            await preprocessDelay(data: data)
+        else {
+            AirshipLogger.trace("Preprocess delay was interrupted, retrying \(scheduleID)")
+            try await processTriggeredSchedule(scheduleID: scheduleID)
+            return
+        }
+
 
         guard
             try await self.store.getSchedule(scheduleID: scheduleID) == data
diff --git a/Airship/AirshipAutomation/Tests/Automation/Engine/AutomationDelayProcessorTest.swift b/Airship/AirshipAutomation/Tests/Automation/Engine/AutomationDelayProcessorTest.swift
index ffe58b509..2b253ac22 100644
--- a/Airship/AirshipAutomation/Tests/Automation/Engine/AutomationDelayProcessorTest.swift
+++ b/Airship/AirshipAutomation/Tests/Automation/Engine/AutomationDelayProcessorTest.swift
@@ -95,7 +95,7 @@ final class AutomationDelayProcessorTest: XCTestCase {
 
         let now = date.now
         Task { @MainActor [processor] in
-            await processor!.preprocess(delay: delay, triggerDate: now)
+            try! await processor!.preprocess(delay: delay, triggerDate: now)
             finished.set(true)
             ended.fulfill()
         }