It seems to me that the problem lies with Integrate with parameters, rather than with Probability. In the following examples the result depends on how we specify the integration region and on the assumptions on the parameter:
dist = MultinormalDistribution[{{1, \[Rho]}, {\[Rho], 1}}];
pdf = PDF[dist, {x, y}];
reg = ImplicitRegion[a >= 0 && b >= 0, {a, b}];
int1 = Integrate[pdf,
{x, y} \[Element] reg,
Assumptions -> -1 < \[Rho] < 1]
int2 = Integrate[pdf,
{x, y} \[Element] reg,
Assumptions -> -1 < \[Rho] < 0]
int3 = Integrate[pdf,
{x, 0, Infinity}, {y, 0, Infinity},
Assumptions -> -1 < \[Rho] < 1]
int4 = Integrate[pdf,
{x, 0, Infinity}, {y, 0, Infinity},
Assumptions -> -1 < \[Rho] < 0]
{int1, int2, int3, int4} /. \[Rho] -> -1/2