diff --git a/Sources/Amplitude/Utilities/EventPipeline.swift b/Sources/Amplitude/Utilities/EventPipeline.swift
index 0639bf1..becc731 100644
--- a/Sources/Amplitude/Utilities/EventPipeline.swift
+++ b/Sources/Amplitude/Utilities/EventPipeline.swift
@@ -17,11 +17,8 @@ public class EventPipeline {
     internal var flushTimer: QueueTimer?
     private let uploadsQueue = DispatchQueue(label: "uploadsQueue.amplitude.com")
 
-    internal struct UploadTaskInfo {
-        let events: String
-        let task: URLSessionDataTask
-    }
-    private var uploads = [URL: UploadTaskInfo]()
+    private var flushCompletions: [() -> Void] = []
+    private var currentUpload: URLSessionTask?
 
     init(amplitude: Amplitude) {
         storage = amplitude.storage
@@ -60,33 +57,58 @@ public class EventPipeline {
         eventCount = 0
         guard let storage = self.storage else { return }
         storage.rollover()
-        guard let eventFiles: [URL] = storage.read(key: StorageKey.EVENTS) else { return }
-        for eventFile in eventFiles {
-            uploadsQueue.sync {
-                guard uploads[eventFile] == nil else {
-                    logger?.log(message: "Existing upload in progress, skipping...")
-                    return
-                }
-                guard let eventsString = storage.getEventsString(eventBlock: eventFile),
-                      !eventsString.isEmpty else {
+
+        uploadsQueue.async { [self] in
+            if let completion {
+                flushCompletions.append(completion)
+            }
+            self.sendNextEventFile()
+        }
+    }
+
+    private func sendNextEventFile() {
+        guard currentUpload == nil else {
+            logger?.log(message: "Existing upload in progress, skipping...")
+            return
+        }
+
+        guard let storage = storage,
+              let eventFiles: [URL] = storage.read(key: StorageKey.EVENTS),
+              let nextEventFile = eventFiles.first else {
+            flushCompletions.forEach { $0() }
+            flushCompletions.removeAll()
+            logger?.debug(message: "No event files to upload")
+            return
+        }
+
+        guard configuration.offline != true else {
+            logger?.debug(message: "Skipping flush while offline.")
+            return
+        }
+
+        guard let eventsString = storage.getEventsString(eventBlock: nextEventFile),
+              !eventsString.isEmpty else {
+            logger?.log(message: "Could not read events file: \(nextEventFile)")
+            return
+        }
+
+        currentUpload = httpClient.upload(events: eventsString) { [self] result in
+            let responseHandler = storage.getResponseHandler(
+                configuration: self.configuration,
+                eventPipeline: self,
+                eventBlock: nextEventFile,
+                eventsString: eventsString
+            )
+            responseHandler.handle(result: result)
+            // Don't send the next event file if we're being deallocated
+            self.uploadsQueue.async { [weak self] in
+                guard let self = self else {
                     return
                 }
-                let uploadTask = httpClient.upload(events: eventsString) { [self] result in
-                    let responseHandler = storage.getResponseHandler(
-                        configuration: self.configuration,
-                        eventPipeline: self,
-                        eventBlock: eventFile,
-                        eventsString: eventsString
-                    )
-                    responseHandler.handle(result: result)
-                    self.completeUpload(for: eventFile)
-                }
-                if let uploadTask {
-                    uploads[eventFile] = UploadTaskInfo(events: eventsString, task: uploadTask)
-                }
+                self.currentUpload = nil
+                self.sendNextEventFile()
             }
         }
-        completion?()
     }
 
     func start() {
@@ -106,12 +128,3 @@ public class EventPipeline {
         return count != 0 ? count : 1
     }
 }
-
-extension EventPipeline {
-
-    func completeUpload(for eventBlock: URL) {
-        uploadsQueue.sync {
-            uploads[eventBlock] = nil
-        }
-    }
-}
diff --git a/Tests/AmplitudeTests/Utilities/EventPipelineTests.swift b/Tests/AmplitudeTests/Utilities/EventPipelineTests.swift
index 7fa6b81..ca2a184 100644
--- a/Tests/AmplitudeTests/Utilities/EventPipelineTests.swift
+++ b/Tests/AmplitudeTests/Utilities/EventPipelineTests.swift
@@ -116,6 +116,35 @@ final class EventPipelineTests: XCTestCase {
         XCTAssertEqual(uploadedEvents![0].eventType, "testEvent")
     }
 
+    func testOneUploadAtATime() {
+        let testEvent = BaseEvent(userId: "unit-test", deviceId: "unit-test-machine", eventType: "testEvent")
+        try? pipeline.storage?.write(key: StorageKey.EVENTS, value: testEvent)
+        pipeline?.storage?.rollover()
+
+        let testEvent2 = BaseEvent(userId: "unit-test", deviceId: "unit-test-machine", eventType: "testEvent2")
+        try? pipeline.storage?.write(key: StorageKey.EVENTS, value: testEvent)
+        pipeline.storage?.rollover()
+
+        let httpResponseExpectation1 = expectation(description: "httpresponse1")
+        let httpResponseExpectation2 = expectation(description: "httpresponse2")
+        httpClient.uploadExpectations = [httpResponseExpectation1, httpResponseExpectation2]
+
+        httpResponseExpectation2.isInverted = true
+
+        let flushExpectation = expectation(description: "flush")
+        pipeline.flush {
+            flushExpectation.fulfill()
+        }
+
+        wait(for: [httpResponseExpectation1], timeout: 1)
+
+        httpResponseExpectation2.isInverted = false
+
+        wait(for: [httpResponseExpectation2, flushExpectation], timeout: 1)
+
+        XCTAssertEqual(httpClient.uploadCount, 2)
+    }
+
     func testInvalidEventUpload() {
         let invalidResponseData = "{\"events_with_invalid_fields\": {\"user_id\": [0]}}".data(using: .utf8)!