It's been a tough 18 months for Boeing (NYSE:BA) investors, with the stock hit first by the March 2019 grounding of the 737 MAX after a pair of fatal accidents and, more recently, by the COVID-19 pandemic.

Shares of Boeing have lost about half of their value so far in 2020 as airlines brace for a prolonged period of weakness brought on by the pandemic by cutting costs and trimming their fleets.

We know Boeing's second-quarter earnings, scheduled to be released before markets open on July 29, are going to be ugly. But there is a lot we don't know about how well the company is holding up through the pandemic, and how management is preparing for the future. Those are issues investors have a lot of curiosity about.

Here are four questions I'll be listening for answers to when Boeing releases earnings and talks with analysts.

When will the commercial segment recover?

Boeing delivered just 10 aircraft in June, and 20 planes in all of the second quarter. By comparison, the company delivered 90 planes in the second quarter of 2019, even with the 737 MAX grounded.

The order book continues to be under assault, with Boeing recording 182 net cancellations in June and 477 for the quarter. The 737 backlog lost 179 planes in June, and companywide Boeing's backlog stood at 4,552 at quarter's end.

A Boeing 787 Dreamliner in flight.

Image source: Boeing

Airbus, by comparison, has a backlog of more than 7,500.

It seems all of the news out of Boeing's commercial airplanes segment of late has been about delays and production slowdowns. The company will reportedly push its 777X debut into 2022, in part due to wavering customer demand, and is scaling back production of both wide-bodies and smaller 737 MAX jets.

Boeing hopes to have the 737 MAX recertified for flight by early October, which would allow the company to resume deliveries and could slow cancellations, but the broader macroeconomic conditions will weigh on the order book for a while.

Boeing at one point had hoped to be producing at least 55 737 MAX planes per month by now, but instead is now hoping to make 72 planes in all of 2020. Forget 2021. I'm growing concerned that the commercial issues will bleed into 2022, if not later, and look forward to any commentary on when management sees deliveries rebounding.

When will the cash bleed stop?

Boeing burned through $4.7 billion in the first quarter, and cash is likely to be a major focus of the earnings call this time around as well. The company's delivery issues are largely to blame for its cash problems, with lots of cash going out the door to support the supply chain and to maintain the hundreds of built but not-yet-delivered jets on its lots, but little cash coming in from customers.

Boeing raised $25 billion in new debt earlier this year, all but assuring it won't run out of money no matter how bad things get. But it added upward of $1 billion in new annual interest payments.

Wall Street expects a loss of $2.30 per share in the second quarter, factoring in compensation payments to customers for delays, severance and separation payments related to restructurings, and pandemic-related issues. I wouldn't be surprised if the $6.6 billion consensus estimate for cash outflow in the quarter proves to be conservative.

At some point, even with the added liquidity, Boeing needs to stop burning through cash. That won't happen in the second quarter, but investors should be listening for color on when management hopes to see the current trends reverse.

Can the defense business save the day?

Boeing's defense business has been largely an afterthought as commercial sales soared higher, but with commercial revenue falling, defense and space are likely to account for nearly one-third of total revenue this year.

A Boeing prototype military drone on display

Image source: Boeing.

The defense business has had its own share of blunders, but over the past two years the company won a series of high-profile competitions that should generate billions in revenue in the years to come. Those programs are mostly in their early stages and are not going to save the day this quarter. Nevertheless, defense is more important to the bull case for Boeing than it has been in a decade.

We know commercial will be bad. It will be interesting to hear how management feels about the space and defense arms of the company, and to what extent those units will help the bottom line in 2021.

Should investors be worried about China?

Boeing's growth in recent years has been due in large part to new-plane sales in emerging markets, and China has been one of the company's best customers. China accounted for nearly 30% of 737 deliveries in 2018, and it has been a sizable part of the overall delivery book in recent years.

Tensions are running high between the U.S. and China, and Boeing's order book could come under fire if a trade war heats up again. Boeing is no stranger to international conflicts, having gotten caught up in tariff battles two years ago and pushing an international fight with Canada over desired tariffs on a small-jet competitor.

If China is looking to make a statement to the U.S., slowing domestic 737 MAX recertification would be a powerful way to do it. With China's Comac attempting to break Boeing and Airbus' duopoly on commercial aircraft by the middle of the decade, the country has every reason to backpedal on Boeing sales.