There are (at least) two ways that technical debts make their way into projects. The first is by conscious decision. Some problems just are not worth tackling up front, so they are consciously allowed to accumulate as technical debt. The second is by ignorance. The people working on the project don't know or don't realize that they are incurring a technical debt. This question deals with the second. Are there technical debts that you let into your project that would have been trivial to keep out ("If I had only known...") but once they were embedded in the project, they became dramatically more costly?
Ignoring security problems entirely.
Cross-site scripting is one such example. It's considered harmless until you get alert('hello there!')
popping up in the admin interface (if you're lucky - script may as well silently copy all data admins have access to, or serve malware to your customers).
And then you need 500 templates fixed yesterday. Hasty fixing will cause data to be double-escaped, and won't plug all vulnerabilities.
One example of this is running a database in a mode that does not support Unicode. It works right up until the time that you are forced to support Unicode strings in your database. The migration path is non-trivial, depending on your database.
For example, SQL Server has a fixed maximum row length in bytes, so when you convert your columns to Unicode strings (NCHAR, NVARCHAR, etc.) there may not be enough room in the table to hold the data that you already have. Now, your migration code must make a decision about truncation or you must change your table layout entirely. Either way, it's much more work than just starting with all Unicode strings.
Unit Testing -- I think that failing to write tests as you go incurs a HUGE debt that is hard to make up. Although I am a fan of TDD, I don't really care if you write your tests before or after you implement the code... just as long as you keep your tests synced with your code.
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