Narrative:

Notified at xa:00 pm that an important flight had to take place; depart as soon as possible. Planned for an xb:00 pm departure. Added engine oil; pre-flighted; got drinks; filed the flight plan...using flight plan go on my ipad. I got the AWOS weather for ZZZ about 30 minutes before actual departure. Since it was dusk I could still see the sky and the ceiling was ahigh overcast moving in - plenty of VMC to depart VFR and pick up the clearance in the air. I was relaxed and not rushed. My friend (another pilot) arrived to fly along and assist.we departed around xb:05 pm. As we turned left to begin the route toward ZZZ VOR; we inadvertently flew into a small cloud; a puff. Then we encountered a couple more. I couldeasily see the ground and surrounding area. As I evaluated whether to climb or descend (it was now totally dark); the other pilot called center to request the IFR clearance. Center reported no clearance was on file. At this point I had climbed above what was now obviously a very thin cloud layer; not solid; and not widespread. I was now clearly in VMC conditions above the layer; could see the ground below it; but knew the real ceiling was somewhere above me and I would not have much time to get the clearance. Yet the flight plan I filed electronically apparently did not submit into the system properly.the controller was helpful and assisted me in getting the flight plan submitted. In a few minutes he issued my clearance and we were on our way. It was my perception that he may havethought I purposely departed without filing a flight plan; instead leaning on ATC to do it as a pop-up. I do not operate this way and have never asked ATC to do this. The controllerwas very professional and did not imply anything. But I am sure they see pilots do this kind of thing all the time. I was embarrassed; but at that point it seemed safer to continue forward in a slow climb and while still marginal VFR (it was very dark) than to try to return and land VFR. Our TCAS showed one other target in the area and it was 2000' or more below us and several miles away. We could also see the lights of the target out the window below us. I don't believe there was any conflict between us and this target at any time.the ceiling had obviously begun lowering near the airport; after I had retrieved the weather. I did not see the cloud deck and therefore was surprised by the inadvertent cloud penetration. Resolution: make sure I get the latest weather and especially at dark; with anything but stars and the moon; get the clearance on the ground before departure. While I was sure I had submitted the flight plan; I apparently had not completed it properly. Later that evening when I checked the website; the flight plan was still there; asif it had not been filed. Resolution: by getting the clearance on the ground prior to departure I would have known the flight plan did not submit properly and I could have corrected it.

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Original NASA ASRS Text

Title: EMB-500 pilot reporting departing VFR with the intention of picking up previously filed IFR flight plan inflight. After inadvertently flying through scattered clouds in approaching darkness; pilot was advised by ATC that the flight plan was never received. New flight plan was filed and clearance issued by ATC.

Narrative: Notified at XA:00 pm that an important flight had to take place; depart as soon as possible. Planned for an XB:00 pm departure. Added engine oil; pre-flighted; got drinks; filed the flight plan...using Flight Plan GO on my iPad. I got the AWOS weather for ZZZ about 30 minutes before actual departure. Since it was dusk I could still see the sky and the ceiling was ahigh overcast moving in - plenty of VMC to depart VFR and pick up the clearance in the air. I was relaxed and not rushed. My friend (another pilot) arrived to fly along and assist.We departed around XB:05 pm. As we turned left to begin the route toward ZZZ VOR; we inadvertently flew into a small cloud; a puff. Then we encountered a couple more. I couldeasily see the ground and surrounding area. As I evaluated whether to climb or descend (it was now totally dark); the other pilot called Center to request the IFR clearance. Center reported no clearance was on file. At this point I had climbed above what was now obviously a very thin cloud layer; not solid; and not widespread. I was now clearly in VMC conditions above the layer; could see the ground below it; but knew the real ceiling was somewhere above me and I would not have much time to get the clearance. Yet the flight plan I filed electronically apparently did not submit into the system properly.The controller was helpful and assisted me in getting the flight plan submitted. In a few minutes he issued my clearance and we were on our way. It was my perception that he may havethought I purposely departed without filing a flight plan; instead leaning on ATC to do it as a pop-up. I do not operate this way and have never asked ATC to do this. The controllerwas very professional and did not imply anything. But I am sure they see pilots do this kind of thing all the time. I was embarrassed; but at that point it seemed safer to continue forward in a slow climb and while still marginal VFR (it was very dark) than to try to return and land VFR. Our TCAS showed one other target in the area and it was 2000' or more below us and several miles away. We could also see the lights of the target out the window below us. I don't believe there was any conflict between us and this target at any time.The ceiling had obviously begun lowering near the airport; after I had retrieved the weather. I did not see the cloud deck and therefore was surprised by the inadvertent cloud penetration. Resolution: Make sure I get the latest weather and especially at dark; with anything but stars and the moon; get the clearance on the ground before departure. While I was sure I had submitted the flight plan; I apparently had not completed it properly. Later that evening when I checked the website; the flight plan was still there; asif it had not been filed. Resolution: By getting the clearance on the ground prior to departure I would have known the flight plan did not submit properly and I could have corrected it.

Data retrieved from NASA's ASRS site and automatically converted to unabbreviated mixed upper/lowercase text. This report is for informational purposes with no guarantee of accuracy. See NASA's ASRS site for official report.