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Yesterday I throttled up for Sky High 2 (SKY777/N4436E) at around 1600Z.
I had to file a couple of flight plans due to some errors I made.

Finally, I was ready, received my clearance and took off.
About 15 NM south of TAS, I was cleared for the LOC/DME into KSKX.

At about 10 NM out of KSKX, the Controller canceled IFR. I switched to CTAF, made my calls and landed. Once on the ground at the ramp, I checked in again with Radar to Close my flight plan.
I expected the Controller to close my flight plan on my request. Instead, the Controller (again) said that IFR was cancelled.

As far as I remember, once IFR is cancelled, the associated flight plan is still active and has to be closed by the Pilot, either on the ground after landing or when the field is in sight.

For some other reasons, I was not able to conduct the second flight, so I have to start over from KABQ anyway.

Could somebody explain why I received two IFR cancellations instead of a confirmation of my request to close the flight plan after my landing at KSKX?

Please review the ATC audio from your flight. What was the exact wording that was used by the controller while you were in the air, on approach into SKX?

Note: This isn't a loaded question. I haven't listened to the audio. I'm asking you to review it and report what you find.

Yesterday I throttled up for Sky High 2 (SKY777/N4436E) at around 1600Z.
I had to file a couple of flight plans due to some errors I made.

Finally, I was ready, received my clearance and took off.
About 15 NM south of TAS, I was cleared for the LOC/DME into KSKX.

At about 10 NM out of KSKX, the Controller canceled IFR. I switched to CTAF, made my calls and landed. Once on the ground at the ramp, I checked in again with Radar to Close my flight plan.
I expected the Controller to close my flight plan on my request. Instead, the Controller (again) said that IFR was cancelled.

As far as I remember, once IFR is cancelled, the associated flight plan is still active and has to be closed by the Pilot, either on the ground after landing or when the field is in sight.

For some other reasons, I was not able to conduct the second flight, so I have to start over from KABQ anyway.

Could somebody explain why I received two IFR cancellations instead of a confirmation of my request to close the flight plan after my landing at KSKX?

Please review the ATC audio from your flight. What was the exact wording that was used by the controller while you were in the air, on approach into SKX?

Note: This isn't a loaded question. I haven't listened to the audio. I'm asking you to review it and report what you find.

Audio Review Western US Radar 1000-1100 as of August 12
Inbound TAS on V83
at 04:50: Center: Cross TAS VOR at 12000. Cleared VOR DME Approach

TAS Outbound on R116:
at 10:50: Center: IFR cancellation ... on the ground (?) ... Radar Service terminated. Frequency Change approved

On the ramp at TAOS:
at 12:53: SKY777: Center. SKY777 on the ground. Please close the flight plan.
at 13:02: Center: IFR cancelation received.

Hope this helps.

Friedhelm

10:50: ATC: "report IFR cancellation...."

He's instructing you to report the cancellation of IFR or initiation of the missed approach.

Then, when you call on the ground later, that is effectively your IFR cancellation, which he acknowledges.

I have an issue with the filing options for the second leg. They are as follows:

File IFR from KSKX to TAS, or
File IFR from KSKX to TAS and include “VFR on top” in the remarks, or
Do not file IFR, simply call ATC and request a “climb to VFR on top at the Taos VOR” and let them issue the clearance. Let them know you plan to climb to 12,500 if you use this option.

From a real world perspective I wouldn’t do any of these. Here’s my breakdown: For the first, Why file just to TAS? You know your destination is DRO, so even if you thought you could go “VFR on Top” and then maybe get into DRO VFR you could plan to cancel IFR once at your en route altitude. Ditto for the second option. As for the third, requesting an IFR climb to altitude is procedurally the same as the first but with none of the benefits of the first.

If you know you flying to DRO and need to climb out IFR but think you might break out at altitude and be able to proceed VFR on Top, then just file IFR SKX to DRO and cancel when in the clear. If the undercast doesn’t clear as you near DRO, then call ATC and request a pop-up IFR descent and approach into DRO

This was designed with real world in mind. The idea is to avoid the altitudes and routing that would be associated with IFR all the way to DRO, hence the short range clearance to get through the local weather, then a VFR segment, then IFR into the destination.

The route we're taking out of the DRO VOR, VFR, is not what you would get for an IFR flight as it's below the minimum IFR altitude for the area.

Understood. But you're assuming that while on the ground at SKX you know what the tops are en route. Skew Ts may give you an educated guess but not a definite answer (unless there is a pilot report). If you may end up having to pick up an IFR route clearance over TAS anyway, why not file for the whole route, then cancel if you're guess about the cloud tops is correct and then proceed until you need to request an IFR descent and approach into DRO?

The routing for a 100% IFR solution involves 13,000ft MEA's, which will actually translate to 14,000ft based on direction of flight (controllers normally try to adhere to that as an extra safety net since airways commonly have traffic in both directions). The pure IFR airway route involves a 12k 41-mile leg, then a 14K 51-mile leg.

The goal of the exercise was to introduce a relatively rare tool (VFR on top and short range IFR clearances) to minimum the altitude foot print and maximize efficiency.

You're right, you could file IFR the whole way, cancel on top, then pick up a new clearance at BRAZO (either pop-up or as 2nd filed flight plan), however, that doesn't bring attention to those new tools. Imagine if the MEA's were a tad higher, or the airway routing was exceedingly long, and, given full payload with partial fuel, resulted in you not being able to meet the IFR fuel requirements to accept the clearance. You'd get to a point where you couldn't accept a full IFR route even if you wanted to. Without knowing about those new tools, you might feel as though you're otherwise out of options.