The terrain around the house makes it almost impossible to do any sort of structured power-based workout outside. The only real option that I can see is to try to match the IF and time while still paying attention to the TSS to meet the goal of the workout. I can easily set up a route and plan my effort without trying to push the TR workout to the Garmin. When the ride is over and it publishes to TR, then I end up with the completed outside ride and the uncompleted TR workout. Is it better to keep the uncompleted workout so that the planned TSS and actual TSS are closer together, or to delete the TR workout?
You can also just associate the TR workout with the Outside unstructured ride. This combines the outside ride and work out into 1 and also increases your Progression Levels. Its not as recommended as just pushing the workout to Garmin and doing it but it works.
Edit: To associate the outside ride with a workout out click on the ride and if there is a TR workout scheduled for that day on the calendar there will be a button that says match ride
In previous posts on this topic, TR has recommended we leave the planned workout in the calendar, but DO NOT associate the two. Once they release the ability to grade unstructured rides, this will solve itself.
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Cheers for that, i never knew that
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I was doing it too. In fact, I sometimes still do, but they say not to. I’m trying desperately to ween myself from my current mentality of jumping through hoops to impact PL’s. 
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I was able to grade the 3 outside rides just like I get asked to grade the inside workouts (easy-race).
Yes, you can grade them, but it won’t impact PL’s unless you associate it with a structured workout.
Yes, I can see that after I associated them, It did impact my PLs for both yesterday’s and today’s rides. It also seems to me that if I decide to a recovery ride when I don’t have anything scheduled, AND decide to do it outside then I should go ahead and insert a recovery workout and then associate the two afterward.
Hey @Redleg94, welcome to the forum! 
There are a few things worth addressing here.
First, although the terrain in your area might seem difficult to accurately perform Outside Workouts, I bet that there are ways to achieve this. Finding the right gearing and the right roads really makes all the difference. We wrote a really great blog post about this. Check out the link below!
Next, I want to stress that simply matching the IF and TSS of any given workout isn’t likely to replicate its specific training stimulus. Structured training is by far the best way to sustainably increase fitness, and this means following the structure to ensure that you’re applying the right amount of stress for the right amount of time day over day, week over week. Oh, and we have another blog post about this too!
If, however, you are planning to ride outside and not follow a workout, I’d recommend keeping this ride file in your calendar to reference the data as you’ve mentioned. It’s a good idea to keep an eye on your TSS total throughout the week and this includes activities of all types. Ignoring non-workout TSS could encourage you to underestimate the stress you’re actually carrying, which could negatively affect your training decisions later in the week.
It’s also just worth mentioning here as a reminder to all that, as @Pbase said, we advise against associating outside rides with TrainerRoad workouts unless you’ve followed the structure of the workout. Falsely inflating Progression Levels in this way will only create misleading data and lead to issues down the road.
We’re working on a feature that will take these unstructured rides into consideration with Adaptive Training and give each activity an effective “Workout Level” that will influence your Progression Levels in the same way as our workouts.
I’d focus on nailing the workouts that you can with accuracy, whether inside or out, and then enjoying any additional riding you’re deciding to do. If you can, keep it easy as often as possible to ensure that you’re well-rested for the hard workouts if gaining fitness is your biggest goal.
It’s all a balance, so take a step back every now and then to make sure that you’re enjoying yourself. It’s supposed to be fun!
Just shout if you have any other questions about any of this. I’d be happy to chat some more! 
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This is probably honestly fine for steady z2 rides.
However, if your effort has not been steady - your power profile is spiky or has intervals, rather than being a flat line - then this doesn’t make sense to do.
I’ll check that blog post, but knowing the terrain around here, even if i were to get in the car and drive somewhere, there just isn’t the consistent flat or uphill for long sustained efforts at a consistent sub-threshold power.
The only rides that I’d consider doing outside are either recovery, where I can find some somewhat flat ground, or endurance rides. For anything that would be in the threshold, SweetSpot or VO2 Max categories, I’m almost forced inside just to be able to hit consistent power numbers. If I’m just riding on effort, then I can do that outside. I’ll most likely continue to do anything other than Endurance rides inside even when the weather turns better just due to time constraints and reserve my outside riding for the weekends when I have more time and flexibility on when and where I ride.
I do understand the value of structured training. Coming from a running background, it’s almost the opposite where trying to do anything other than steady efforts inside is almost because the treadmills thati have had access to aren’t responsive enough to replicate the pace changes that you see from short, hard efforts.
If I can’t replicate the scheduled workout but what to take advantage of the ability to ride outside, what is the best way to get the right effort and effect for that day? Also, how do I make sure that I’m not negatively affecting the following weeks training? IOW, if I go on the group ride and end up blowing out my legs, will TR take that into account and adjust the hard efforts downwards if required to keep them productive and achievable? OR is that really part of my self assessment and adjusting the workout myself if my legs just feel overly tired?
Any outside ride around is mostly going to have a somewhat spiky power profile, regardless of the effort that goes into it and with average power and heart rate solidly in Zone 2.
Yes, just like a z2 ride done on the trainer not in resistance mode.
I was more referring to something where the NP is significantly difference than the average power, due to say, a bunch of time spent at much higher or much lower power.
Hey @Redleg94,
Thanks for all of the info.
You’d be surprised what some determined TR athletes can accomplish with Outside Workouts! 
If you’re able to find a terrain steady enough for Recovery or Endurance workouts, I’d say those are good enough for Sweet Spot and Threshold as well. You can always use Workout Alternates to find workouts with shorter intervals if need be. The same goes with VO2 Max. Often times you really only need an area for a < 5-minute interval.
Either way, working out on the trainer is great, too!
Ah, yes, running intervals. Those are fun. 
This is exactly why so many do those workouts outside, though! There are no limitations from the “dreadmill” that way! 
As far as dealing with your unstructured rides, as of now, we aren’t going to pay attention to that group ride that blew your legs out. It’s up to you to manage your unstructured efforts as you see fit and approach your training plan wisely.
With that being said, one of our biggest priorities right now is a feature that will analyze all of the activities on your TR calendar and make adjustments on the fly when it thinks that you need to turn things down due to the risk of fatigue.
Let me know if this helps and if you have any other questions.
Happy training!