As you put in the your "Also" section, after your first left shift of 1 bit, a DOES reflect -1000 as expected.
The issue is in your cast to unsigned int. As explained above, the negative number is represented as 2's complement, meaning the sign is determined by the left most bit (most significant bit). When cast to an unsigned int, that value no longer represents sign but increases the maximum value your int can take.
Assuming 32 bit ints, the MSB used to represent -2^31 (= -2147483648) and now represents positive 2147483648 in an unsigned int, for an increase of 2* 2147483648 = 4294967296. Add this to your original value of -1000 and you get 4294966296. Right shift divides this by 2 and you arrive at 2147483148.
Hoping this may be helpful: (modified printing func from Print an int in binary representation using C)
void int2bin(int a, char *buffer, int buf_size) {
buffer += (buf_size - 1);
for (int i = buf_size-1; i >= 0; i--) {
*buffer-- = (a & 1) + '0';
a >>= 1;
}
}
int main() {
int test = -500;
int bufSize = sizeof(int)*8 + 1;
char buf[bufSize];
buf[bufSize-1] = '\0';
int2bin(test, buf, bufSize-1);
printf("%i (%u): %s\n", test, (unsigned int)test, buf);
//Prints: -500 (4294966796): 11111111111111111111111000001100
test = test << 1;
int2bin(test, buf, bufSize-1);
printf("%i (%u): %s\n", test, (unsigned int)test, buf);
//Prints: -1000 (4294966296): 11111111111111111111110000011000
test = 500;
int2bin(test, buf, bufSize-1);
printf("%i (%u): %s\n", test, (unsigned int)test, buf);
//Prints: 500 (500): 00000000000000000000000111110100
return 0;
}