One of the real warning signs of a bad company can also be the sign of an undervalued company about to make a recovery. And determining whether this factor is a sign of good or bad things to come is really hard, because it comes down to the question of whether a company has too much debt or not when it clearly already has a lot of debt.

This is the world of PIK. Payment-in-Kind (PIK) instruments have always been a bit of a mixed bag in corporate finance. On one hand, they offer companies a way to conserve cash by paying interest with more debt or equity rather than cash. On the other hand, they can quickly turn into a financial mess if mishandled. PIKs come in a couple of flavors—traditional and synthetic—and while they serve the same basic purpose, the way they operate and the risks they present can be quite different.

Traditional PIKs are the more straightforward of the two. Imagine a company that owes interest on its debt but doesn’t have the cash to pay it. Instead of defaulting, it issues more debt or equity to cover the interest payment. This means the company’s debt load increases over time, but it gets to keep its cash on hand to deal with other pressing needs. You see these a lot in leveraged buyouts or when a company’s cash flow is tight, and they can be a smart move if there’s a reasonable plan for paying down the increased debt later on.

Synthetic PIKs are where things start to get a little more complex—and potentially risky. These don’t involve issuing additional debt or equity directly. Instead, they use financial derivatives or structured notes to mimic the effect of a PIK. For example, a company might enter into a swap agreement that defers its interest payments, or it could use other instruments that push obligations into the future without adding new debt. This approach can be tailored to specific needs, like optimizing tax outcomes or making a balance sheet look better on paper.

But the real issue with synthetic PIKs is that they can be incredibly opaque. While traditional PIKs have pretty clear terms, synthetic ones might hide the true level of risk behind layers of financial engineering. This makes it harder for investors to understand what they’re really getting into—and harder for regulators to keep track of what’s going on.

So, what makes a PIK “good” or “bad”? It often comes down to intent and execution. A well-structured PIK can be a lifeline for a company going through a rough patch, allowing it to keep the lights on and fight another day. But when PIKs are used to cover up deeper financial problems or to load up a company with unsustainable levels of debt, that’s when trouble starts. Synthetic PIKs, in particular, are prone to abuse because their complexity can make it easy to push debt into the future without a solid plan for repayment.

In some cases, companies might use these instruments to finance risky acquisitions or pay out dividends, which can lead to short-term gains but leave the company teetering on the edge of a debt spiral. The danger is that if the company’s fortunes don’t improve as hoped, the compounded debt from these PIKs can quickly become unmanageable, leading to financial distress or even bankruptcy.

So, while PIKs can be useful tools, they require a careful touch. Whether traditional or synthetic, the key is to use them responsibly, with a clear strategy for managing the growing debt load they create. Otherwise, what might seem like a temporary solution could end up being a long-term problem.