I've had this bag since 10/2018 and have been using it daily for work & personal use since then - current review is being written on 2/2021. It's a lot of money for a bag, but I'd say it was very worth it for me. Here's some info on my experience more than 2 years after purchase:

Durability:
- This bag has held up very well overall. Waxed canvas and leather are wearing in all the right ways. All leather on this bag starts stiff, but wears in. This is particularly noticeable in the shoulder strap when you first get it.
- I thought the thick leather pad on the back of the bag was a little much, but it is absolutely necessary to protect the canvas from belts, badges, and jean rivets. The leather pad is quite scuffed up at this point, but in a good, worked-in way.
- I'm getting ready to re-wax this for the first time as the bag is looking a bit faded since I first got it. In fact, coming to saddleback.com to look for care instructions is what lead me to write this review!

Quality:
- The leather and canvas pieces are all high quality, and are joined securely with heavy gauge thread and rivets
- The stitching in points where multiple pieces of canvas meet is a little sloppy here and there. Namely the bottoms of the pockets. But the material is very thick at these points and I suspect that making clean joints is a challenge. It's just neatness complaint, no signs of compromised durability at all. I singe stray threads off with a lighter when I notice them.
- The O-rings that allow you to clip on and off the removable shoulder strap are the lightest-duty piece of hardware on this bag. They are not the same type of metal that you see in the clips and D-rings on other parts of the bag. Over the years, my O-rings have bent and deformed a bit, but I think it will be several more years before they need to be replaced.
- All metal gear on this bag, besides the o-rings mentioned above, is still shiny, strong, and in great condition.

Design:
- Form factor is great, it's exactly the right size for an every day bag.
- Fold-down front pockets are excellent. I was on the fence about these, but it's a great design and very practical.
- The back laptop slot can fit most any ultrabook with a screen >=14" that I've found. 15" Macbook pro's fit as well ( but barely) thanks to the fact that they're so thin.
- I also like that the laptop pocket stops ~1" before the bottom of the bag. This means that you can set your bag down and not worry about the laptop impacting the ground.
- Side pockets (on the far left and right) are nice, but they don't comfortably hold a phone (I use an iPhone 11 w/ slim case), which is what I envisioned their use as. These pockets are also too deep to carry small, loose items as they fall to the bottom and are a challenge to get at without taking the bag off and squeezing your hand in. I now use a tall rechargeable battery pack in one (i can access the ports without removing it), and a leatherman clipped onto the pocket wall of the other. These could also be good for quick-access pens and pencils as long as they have a clip to keep them from falling in.
- The fastening mechanism for the main flap is unique and does take some getting used to if you want to open and close this quickly. That being said, you get used to it quickly and it feels like a very secure mechanism for a bag that I have hanging off my back. It would probably be a challenge for someone to open the bag and swipe something from you when you're using this.
- The main shoulder strap is a cool design, but I wish it was designed for a smaller size adjustment. I'm 6'1" and find that when the strap is adjusted to the correct length, the leather pad doesn't align with my shoulder like I'd want. It ended up being fine, but it was an initial concern for me as I prefer to wear this bag so that it hangs at my lower back/upper butt. Most demo videos for this bag show the wearer with the bag at thigh-level, and I don't think this is a realistic usecase for most.
- The leather handle design on the top is good, but it tends to scrunch the top of the bag up when you're using it to carry a loaded-up pack. I wish they used a piece of support leather (sewn into the inside) that was thicker, like the one used on the outer back of the bag.

What do I carry:
- 13" macbook air [laptop slot]
- leather folio notebook for paper, business cards, etc [main area]
- 32 oz nalgene [main area]
- Readywares Waxed Canvas Pencil Case Pouch (8.5"x4") filled with writing utensils, ruler, etc. [main area]
- semi-rigid hard case (Smatree Hard Case A90) for electronics, cables, chargers (macbook & iphone), USBs drives, etc [main area]
- pocket moleskine notebook [space behind foldover pockets]
- keys, wallet, phone, glasses, etc. [foldover pockets]
- battery pack & leatherman [left & right side pockets, respectively]
- with all of this, I still have some more room in the main area and an open space behind the other foldover pocket for new/temporary items.

miscellaneous notes:
- the embossed build date on the back leather pad is a cool touch
- the bottom leather piece can hide a wallet-sized Tile tracker in the cavity between the rivets. I currently have one on order as I've recently realized how screwed I would be if I lost this bag. Tile can track items in "lost mode", so I'm hoping this will help me sneakily track down a lost or stolen bag.
- I haven't needed to contact support since I ordered this bag, although I have bought a satchel for the gf and a leather wallet for myself. Both of those were equally high quality.

Its a great bag, but the 100 year guarantee will need to come into play, because it has developed a whole at the back where the computer goes - the bag works hard, but the leather is definitely a little longer lasting - these are superior products, don't get me wrong .... the best ever, but shoot for the leather if you are serious

I'm extremely happy with this. I wasn't sure I'd love the leather pads on the bottom and side that give the bag shape, but they are the features I never knew I wanted. Not only do they make the bag stand up when you set it down, they allow the bag to slide against your legs with little friction. This makes walking less clunky than with other messenger bags.

Fantastic quality! I use it work on the weekdays and it's my baby bag when needed. No more flower bags! Love it. Goes with my wallet and note pad from saddle back take it everywhere. I'll always buy from saddle back leather.

I have owned this bag now for around 3 years I guess - looks the way it did when I bought it, and it goes to work with me everyday - tuff, rugged and practical for any business mode. It genuinely might last 100 years.