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Is it possible for HTTP server to receive requests out of order even if they are sent sequentially?

(This discussion might not be specific to C#...)
I have a C# method SendMultipleRequests that sends HTTP POST request 10 times sequentially.
Is it possible for the server to receive requests out of order?
If my understanding is correct if the requests are sent concurrently (without await), the server could receive requests out of order, but in the example below it needs to wait for the response to be received at the client before sending next request, so the server will receive requests in order.
public async Task SendRequest(int i)
{
// definition of endpoint is omitted in this example
var content = new StringContent($"I am {i}-th request");
await HttpClient.PostAsync(endpoint, content);
}
public async Task SendMultipleRequests()
{
for (int i = 0; i < 10; i++)
{
await SendRequest(i);
}
}

with await your app will wait for the task returned by PostAsync to finish before it issues the next request - see the docs for postasync where it says “This operation will not block. The returned Task<TResult> object will complete after the whole response (including content) is read.” - using await will mean that you will only issue the next request after you I’ve read the content of the previous response
If you remove the await then your code will queue up ten tasks and start working on them all in some undefined order. The server will see requests in an unspecified order. This may be further exacerbated by the fact that the requests may take different routes through the internet, some slower. If you remove the await then you should capture the returned task into a list, then you can use something like await Task.WhenAll(list) to wait for them all to complete (unless you really want to fire and forget in which case you can assign them to the discard _ = client.PostAsync... but keeping the task allows you to discover and deal with exceptions that arose)

Calls to an API fails after some time when multiple users are logged in and using the application. Is there a way to solve this?

I am making some calls to an api that syncs and saves appointments to/from my application and mail agenda which is most commonly Outlook mails. The calls to the api are made from a web application and it is working fine for some time but then immediately after a few hours, the calls are failed. This continues for some time and starts to work again after some time.
The DefaultConnectionLimit was set to 100 in the beginning and during this scenario, the process stopped working after some time (Say 30 mins to 1 hour). Then DefaultConnectionLimit was set to 20 and in this case, it worked fine for 3-4 hours and stopped working after that. I don't know if this is the actual cause but just mentioning.
The code where the call to the api is made from the web application is mentioned below :
public bool SyncNewAppToExch(string encryptedAppSyncDetails)
{
try
{
string result = string.Empty;
JArray paramList = new JArray();
paramList.Add(encryptedAppSyncDetails);
var emailApiUrl = ConfigurationManager.AppSettings["emailApiUrl"].ToString();
Uri baseAddress = new Uri(emailApiUrl);
var url = "/api/EmailProcess/ManualSaveAppointments";
HttpClient client = new HttpClient();
client.BaseAddress = baseAddress;
client.DefaultRequestHeaders.Accept.Clear();
client.DefaultRequestHeaders.Accept.Add(new MediaTypeWithQualityHeaderValue("application/json"));
Task.Run(() => client.PostAsJsonAsync(url, paramList)).Wait(5000);
var responseMessage = true;
if (responseMessage)
return true;
else
return false;
}
catch (Exception ex)
{
return false;
}
}
The exception that follows the api call failure reads :
Exception : System.AggregateException: One or more errors occurred. System.Threading.Tasks.TaskCanceledException: A task was canceled. --- End of inner exception stack trace --- at System.Threading.Tasks.Task1.GetResultCore(Boolean waitCompletionNotification) at System.Threading.Tasks.Task1.get_Result()

If you are making a new HttpClient object each time you want to make a call, you are not using it appropriately. HttpClient may continue to use sockets even if it is no longer being used and this will likely cause socket exhaustion under load. You can see more on this topic here
You should create a single instance and reuse it. If you are using .Net core it would be a better idea to use the HttpClientFactory.
In addition, using Task.Run to call an async method is not wise. You are setting yourself up for a deadlock. It would be much better to mark your method as async and await, if possible. Since you are effectively doing fire and forget, the way you have done this if your App Domain shuts down this work will be lost.
If you need to do this, you should at least consider registering your task as such:
HostingEnvironment.QueueBackgroundWorkItem(ct => SendMailAsync(user.Email));
The short answer is that it is difficult to say what your issue is, it could be one of several problems.

HttpClient cancellation doesn't kill underlying TCP call

I'm trying to set a default timeout for my HttpClient calls to 5 seconds.
I've done this via CancellationTokenSource.
Here's the pertinent bit of code:
var cancellationToken = new CancellationTokenSource();
cancellationToken.CancelAfter(TimeSpan.FromSeconds(5));
var result = _httpClient.SendAsync(request, cancellationToken.Token);
Works as i expected in terms of the calling code getting a "Task was cancelled" error (i tested in a .NET 4.7 console app), but i noticed in Fiddler the request was still running for 1 minute, until it finally gave up:
Can someone explain this behaviour?
I would expect the underlying request to also get cancelled when the cancellation is triggered.
_httpClient is instantiated like: new HttpClient { BaseAddress = baseAddress }
I know there's the the Timeout setting, but not sure if I should be using that or cancellation tokens? My guess is Timeout is for the non-async/await cases?

As Damien said in the comments, HttpClient re-uses connections as much as possible, hence the reason why the connection is not closed on cancel.
When canceling a request like that, the HttpClient will just stop sending/receiving data to/from the other end. It will not send anything to inform the other end that it was cancelled. So the timeout you see of 1 minute depends on the behavior of the other end of your connection.
Also, if you want to cancel each request after 5 seconds, you can as well set the Timeout property of _httpClient to TimeSpan.FromSeconds(5). The behavior will be exactly the same (a TaskCanceledException will be thrown if the other end doesn't respond within 5 seconds).

If anyone is interested, you can try the following approach to applying your own timeout per HttpClient request. It seems to work for me, restricting the SendAsync() to 2 seconds and returning immediately when the timeout occurs:
private async Task<HttpResponseMessage> SendAsync(HttpRequestMessage request, TimeSpan? timeout = null)
{
if (timeout is null)
{
return await _httpClient.SendAsync(request);
}
else
{
using (var cts = new CancellationTokenSource(timeout.Value))
{
var sendTask = _httpClient.SendAsync(request);
while (!sendTask.IsCompleted)
{
cts.Token.ThrowIfCancellationRequested();
await Task.Delay(10).ConfigureAwait(false);
}
return await sendTask.ConfigureAwait(false);
}
}
}

Wrapping both cpu-bound/io-bound long-running code into (async) Task

Consider the simple MVC5 controller:
public class DocumentsController {
// ctor code is omitted
[HttpPost, Route("api/documents/request/stamp={stamp}")]
public ActionResult RequestDocuments(string stamp) {
var documents = this.DocumentsRequestService.RequestByStamp(stamp);
return new JsonResult(documents);
}
}
The DocumentsRequestService does these things internally:
it sends a request to a dedicated MSMQ-queue (let's call it M) AND synchronously waits for an incoming message at the M's response queue:
using(var requestMessage = new Message()) {
requestMessage.Body = documentStamp;
requestMessage.Recoverable = true;
requestMessage.Label = "request";
requestMessage.ResponseQueue = this.requestedDocumentsResponseQueue;
requestMessage.Formatter = new XmlMessageFormatter(new Type[] { typeof(String) });
// send request
this.requestedDocumentsQueue.Send(requestMessage);
// synchronously wait for response
var responseMessage = this.requestedDocumentsResponseQueue.Receive();
if(responseMessage.Label.EndsWith("success")) {
return new DocumentsRequestResult(
success: true,
matches: parseMatchesList(responseMessage)
);
}
return new DocumentsRequestResult(
success: false,
matches: Enumerable.Empty<DocumentsRequestMatch>()
);
}
the consumer (Windows Service) of that message makes a specific api call. By saying 'specific' I mean that we use a third-party means to do that. This call is synchronous and quite long. When the processing ends the consumer sends a response message to the requesting message's response queue.
when response arrives at the M's response queue it's a time to parse and return the results to the controller.
From the end user's perspective this task should be blocking, or at least it should look like blocking.
As far as I understand running a Task makes use of parallelization. Whereas using the async-await pair makes the running task asynchronous. It could be helpful if several tasks would run in parallel.
Is it reasonable/possible to incorporate with Tasking/Asynchrony in my case? If yes, then where do I start?

The "asynchrony" of a network call is transparent to the caller. It doesn't matter to the caller whether the implementation is synchronous or asynchronous. Put another way, from a client's perspective, it's always asynchronous.
For example, the HTTP client couldn't care less if RequestDocuments is synchronous or asynchronous; either way, the HTTP client will send a request and receive a response some time later (i.e., asynchronously).
Similarly, the HTTP web server doesn't care whether the Win32 service is implemented synchronously or asynchronously. It just knows that it puts a message on a queue and some time later (i.e., asynchronously) it gets a response message from the queue.
As far as I understand running a Task makes use of parallelization. Whereas using the async-await pair makes the running task asynchronous.
Sort of. Task can be used for either asynchronous or parallel code, a fact that has caused much confusion. However, Task Parallel Library constructs such as Parallel and PLINQ are firmly in the parallel (non-asynchronous) world.
It could be helpful if several tasks would run in parallel.
I believe "concurrently" is the appropriate term here.
First, note that ASP.NET gives you a considerable amount of concurrency for free. If you want to make each request internally concurrent, then you can do so fairly easily via Task.WhenAll. For example, you can change your DocumentsRequestService call to be asynchronous (assuming your message queue API supports async calls):
using(var requestMessage = new Message()) {
...
// send request
await this.requestedDocumentsQueue.SendAsync(requestMessage);
// asynchronously wait for response
var responseMessage = await this.requestedDocumentsResponseQueue.ReceiveAsync();
...
}
Then you can call it multiple times simultaneously from a single controller action as such:
public async Task<ActionResult> RequestDocuments(string stamp1, string stamp2) {
var task1 = this.DocumentsRequestService.RequestByStampAsync(stamp1);
var task2 = this.DocumentsRequestService.RequestByStampAsync(stamp2);
var documents = await Task.WhenAll(task1, task2);
return new JsonResult(documents);
}

Sending multiple requests in any order but no more that 1 request/second

In my c# wpf application when a user presses a button I need to send to a server 10-20 requests. They can be sent in an arbitrary order but there has to be at least 10 of them because the server returns the results paginated.
Each client (my c# is a client) has an apy key and server can only handle 1 request per second per a certain client, otherwise the server returns an error.
How can send those requests properly? Should I necessarily use async and await? And can I send them in parallel and how? Doesn't async in this case means that they'll be sent in parallel?
And, how can I ensure that only 1 request per second is sent? I gathered it's not good to mix the threads, which is Thread.Sleep(1000) for my case, and async/await.

So, you could create a bunch of tasks that stagger the job by a second each time.
Something like:
List<Uri> uris=new List<Uri>(); //fill with uris
var tasks = uris.Select(async (u, i)=>{
await Task.Delay(TimeSpan.FromSeconds(i));
using(var wc = new WebClient())
{
return await wc.DownloadStringTaskAsync(u);
}
});
var results = await Task.WhenAll(tasks);