For a single function, Conditioning of a Problem measured how input errors grow. For $A\mathbf{x} = \mathbf{b}$ the same role is played by one number built from Vector and Matrix Norms and the inverse: $$\kappa(A) = \lVert A\rVert\,\lVert A^{-1}\rVert,$$ with the norm named when it matters, as in $\kappa_\infty(A)$. Always $\kappa(A) \ge 1$.
🔑 Key idea
If $\mathbf{b}$ changes by $\delta\mathbf{b}$, the solution changes by $\delta\mathbf{x}$ with $$\frac{\lVert\delta\mathbf{x}\rVert}{\lVert\mathbf{x}\rVert} \le \kappa(A)\frac{\lVert\delta\mathbf{b}\rVert}{\lVert\mathbf{b}\rVert}.$$ The same bound links a residual $\mathbf{r} = \mathbf{b} - A\tilde{\mathbf{x}}$ to the error in $\tilde{\mathbf{x}}$: a tiny residual can hide a large error when $\kappa$ is large. Roughly, $\log_{10}\kappa$ digits are lost.
💡 Why it works
From $A(\mathbf{x} + \delta\mathbf{x}) = \mathbf{b} + \delta\mathbf{b}$ we get $A\,\delta\mathbf{x} = \delta\mathbf{b}$, so $\lVert\delta\mathbf{x}\rVert \le \lVert A^{-1}\rVert\lVert\delta\mathbf{b}\rVert$. Also $\lVert\mathbf{b}\rVert = \lVert A\mathbf{x}\rVert \le \lVert A\rVert\lVert\mathbf{x}\rVert$, so $\frac{1}{\lVert\mathbf{x}\rVert} \le \frac{\lVert A\rVert}{\lVert\mathbf{b}\rVert}$. Multiply the two inequalities. For the residual, $\tilde{\mathbf{x}}$ solves $A\tilde{\mathbf{x}} = \mathbf{b} - \mathbf{r}$ exactly, so $\delta\mathbf{b} = -\mathbf{r}$.
Nearly parallel lines: a tiny change in b moves the crossing a long way, and a point far along the lines still almost satisfies both equations.
The $10 \times 10$ Hilbert matrix, $h_{ij} = \frac{1}{i + j - 1}$, has $\kappa_2 \approx 1.6 \times 10^{13}$. About how many correct digits should we expect when solving with it in double precision?
Data errors near $10^{-16}$ can grow by $\kappa$: relative error up to about $1.6 \times 10^{13} \times 10^{-16} \approx 2 \times 10^{-3}$.
So only about 3 correct digits, even with a stable method like elimination with partial pivoting.
Answer: about 3
Computing $A^{-1}$ just to find $\kappa$ would cost more than solving the system, so libraries estimate $\kappa_1(A)$ cheaply from the $LU$ factors and report it next to the answer. A few values to keep in mind: $\kappa = 1$ for the identity and, in the 2-norm, for every orthogonal matrix; $\kappa = \infty$ for a singular matrix; and a rough rule that a computed solution has about $16 - \log_{10}\kappa$ correct digits.
⚠️ Common mistake
Trusting a solution because its residual $\mathbf{b} - A\tilde{\mathbf{x}}$ is tiny. That only says $\tilde{\mathbf{x}}$ nearly satisfies the equations; if $\kappa(A)$ is large, nearly satisfying them is compatible with a large error. Another trap: a small determinant does not mean ill-conditioned ($0.1I$ has determinant $10^{-n}$ but $\kappa = 1$). Check $\kappa$, not $\det$.
Practice
Pass with 3 right answers, the last 2 in a row. Each right answer earns 3 XP.
Tobin A. Driscoll and Richard J. Braun, Fundamentals of Numerical Computation (University of Delaware, free online edition): chapter "Square linear systems", section "Conditioning of linear systems"
MIT OpenCourseWare 18.335J, Introduction to Numerical Methods: lecture notes on condition numbers of matrices