It depends on the company, their integrated product line and their customer base.
Some companies have an ingrained culture, so they insist on using older methods, even in the face of reasoned technical arguments for the upgrade. Some companies are progressive and support updating new compilers and standards whenever it makes sense (and, conversely, support sticks to older methods when it makes sense). Some companies are so inclined to accept the latest trend that they use unproven technologies and endanger the stability of their products.
Some embedded products use specific hardware components that are no longer manufactured and for which there is no low-cost alternative available through a combination of newer hardware or software. For example, with hard real-time systems, there may be obsolete equipment that meets critical time constraints, but new equipment cannot be easily obtained, which meets the original requirement.
Some embedded products are highly critical (security critical, critical, etc.) with an active regulatory body that insists on providing solid technical evidence before the update is approved (and the delegate who signs such an update without documented evidence will be legally responsible, if something goes wrong in the field - for example, the system kills someone due to a time error). This documentation can be very expensive to produce. A company with such a product may be more cost-effective to adhere to an older development environment (accepted by the regulator). To pay several million dollars to justify an update for a newer compiler, the tendency to stir up the desire of the company to fork out for the creation of new evidence that justifies the use of the new compiler.
Ultimately, in order to sell a product, you must convince a paid customer to pay for it. If a large percentage of customers of the old system do not want to pay for the upgrade - after all, the existing system works fine - there is no excuse for the seller to upgrade - unless they can make the change neutral for the client (which is often difficult to achieve when updating a critical embedded system if the supplier does not want to absorb a lot of costs). Similarly, a key customer could actually pay for the development and then maintenance of the existing system, and may believe that continuing to pay for the maintenance of the existing system is a better value for money than paying for the upgrade, and in the process of providing evidence that it works as needed.
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