Booked in I originally for SFO-BOS on the redeye and back on the immediate return flight (it's hard to say no to MRs with the 50% bonus). Then, of course, they updated their schedule and nixed the redeyes, so I had to now spend the night in BOS (arriving around 11pm and return departure at 8am). I asked to be rebooked out of OAK as it's 3 miles away and I needed about 1200 more miles for MVP Gold (new itinerary: OAK-SEA-BOS with reverse return routing).

Checked in for both legs with seats selected (OAK-SEA was 11:30am, SEA-BOS about 3pm). Four hours later I got a notification saying my OAK-SEA flight was cancelled (the explanation later given was "aircraft damage") and they're working on rebooking me. I waited to see what this would be--it took about 40 mins--knowing there was a 7am OAK-SEA. NOPE! The new routing was OAK-PDX (overnight) then the next day, PDX-SEA-BOS, getting in at 4pm--which was well after my 7am BOS-SEA departure time.

Long story short, after waiting 2 hours(!!) for a callback from the MVP line the agent informed me that while she could get me on the earlier OAK-SEA flight in first class, there was only premium left on SEA-BOS--the system had cancelled my confirmed flight and made my seat available (to presumably free upgrades). She offered a refund on the fare difference, but since I had booked with the discount code offered in January I figured it wasn't going to amount to much. I only paid $393 for the rt to begin with.

Ultimately ended back up on the SFO-BOS flight to remain in first class (with $15 additional for off-airport parking; I can park at OAK for free).

A few days later, the exact same thing happens on the exact same OAK-SEA flight (aircraft damage again) on an identical itinerary that I had also rerouted from an original SFO-BOS trip (this time as a saver fare). I knew better than to wait for the system to rebook me, so I didn't hesitate to call the MVP line and immediately connected with an agent. I explained that I wanted to just be put on the 7am OAK-SEA flight so I could keep my SEA-BOS leg, and they did just that. I hung up thinking it was settled...but NOPE again! I get an email from the system a few minutes later rerouting my just-updated itinerary to OAK-SEA at 6pm then SEA-BOS the following morning. Again, conflicting with my return flight!

I got this rectified on the phone again. Wrote a long message to Alaska via the Alaska Listens site and received a response exactly 2 weeks later: multiple apologies and a $150 discount code.

Not sure I'm entirely satisfied with this, but it seems like the going rate. I'm considering asking for the added miles lost when I went direct (though this was my original routing). At least they've brought the issues about their system failing to look at earlier flights on multi-leg journeys and also failing to look at return legs when rebooking automatically.