Password hashes are designed so that even small changes in text result in nearly random results. Once you add a salt, which all password hashing schemes should use, even if you used the same password, the hash would be different.
It is not a good idea to store sensitive data in your iCloud, as Apple still own your private key.
I recommend you to use Cryptomator to encrypt your cloud files.
Otherwise, there are many alternatives with zero-knowledge feature you can use, such as CryptPad and NextCloud.
Using multiple rounds of hashing effectively increases the odds of a collision.
But not by much.
Let's say your hash function has X possible outputs, with equal probability:
The chance of getting a collision after 1 round is 1/X.
The chance of getting a collision after N rounds is lower than N/X.
Since modern algorithms have a very large X, way larger than ...
The credentials for Microsoft accounts are more complicated than simple NTLM. If you're using a Windows Hello PIN to log on (which I believe is the default now) the underlying NTLM hash returned when dumping credentials will not necessarily be correct.
Instead, you need to crack the WINHELLO hash. There's some background on doing this here. Hashcat supports ...
There isn't really an off-the-shelf way to do this, at least without a pretty complicated mask rule in hashcat, but it's trivial to write up some code to do it.
Here's some C# that very quickly builds a wordlist using the scheme you described:
IEnumerable<string> Mutate(string input);
static class MutatorExtensions
You are correct that MD5 is not a good solution. If you want to stop offline brute force attacks, PBKDF2 or similar is a much better choice. But, as you have noted, there is a problem: Each generated hash is different. This is because of the salt, that is picked at random for each hash.
In the case of passwords, you look up the right row with the help of an ...
They both implement the same algorithm, so it's not like one can be faster than the other. Use whichever tool is available on whichever platform you use.
In Windows one uses certUtil as
certUtil -hashfile <PATH_TO_FILE> <HASH_ALGORITHM>
and, available hash algorithms are MD2 MD4 MD5 SHA1 SHA256 SHA384 SHA512. These are different ...