PowerShell: Random Password Generator

There are many really good tools capable of generating random passwords with different complexity and purposes. Some of them are integrated in password managers, some embedded in the browser others available programmatically from the cli with no need to use an online password generator.

I guess there are several thousands functions or blog posts on the internet around this topic, but I think that I can add some interesting information that will be useful to everybody at any level of experience, so let’s start!

PWGEN

My absolute favourite is pwgen that creates a lot of possible passwords meeting my needs , e.g with these options secure, unambiguous and containing symbols with the exact length of 10 characters.

$: pwgen -sBy 10
Y+dJ4FH>7F Ppfff]M7'3 c~T3MP)eiR @4XA@,cjd/ <ax,^)-:T4 }C4yPpUe=: 7&,4Jpc?j*
&7@JEE(~<e ^a{X:C4A*r Ra|u7xX{&a /]T~-$3HH( +CHkYTjr$4 x3>|kvK{$C }u`X|LJ\P4
,<9'\<z;"W vsC'abp*3u !@9/nwq<E! AM)H#r9@(# "+iPb{,3|; 4X9Ea<qgTV =mC/_F39kq
}]|Tn3|#/P g[UJa-k9]& 9P#>V$~A(t v+v.9em@EL <nXP4RUnrT d(W\,%9?~x d$.e4Ni;pH
z!w3w$EU9_ a$3nPd`Xcg ?Ep7VdL&(L Prt^N97[vT M"b~VL?:9n )3EXWfH@N| W;3\%nPpx*
;4pm.#o]LH qH$>TV_p94 tAP!{j(9=j 3Aqu@9)+vv Le]7?C'moT R4d.q\7;~k {Mb|W'Wr{4
\>z94VCNTe Vh9)/H.NAd F@W@f7]]v$ |Les`!\}Y3 'c]Ws4L4?f ,H`9i,&>f, /pm4Ldd;>_
kC#4EhR.tn .9goCTLFz~ A[&j97>`J| %4`7%rU?F] e{):n&4!4X )M7<|XaUR" /:_3h%Lh~c
3g%JAeqppg E3$X,?Cmu\ =PH"7Vg+_L r9NjK\n7Hk V9n@+!~%'h 4v#HcX:i%? h%4Pqeh?7)
h\7'#ML-t& Fe=C4U\:4, |77!fk<E\s ,3@xn|U)`Y W.qYRAq'3o i}u,{3M'Ls +Y9TuF]~ck
@v4}_Nc&gd ,pysKWk7`` KN^f4HJ^[q }7]dx9Y^u' "e-hkU'w#3 ,#7TrkysWC ot:R]yX_/7
XCg3&PiEnj hRR*\V]z3j tX?>+9!?dP +c"$?hzAE7 X3sRs+M?E= a%T|w4#AfA x)ncj_$7RM
F%&)kq)v9N }a4LVsd|w) oU%$wmL+/7 {Xi7gko{}_ WA9`c^ptFb z@~?+"4?)A L+sfx_HEd4
H}r-M7=M]' >x^<j\[4HE %y~X3eh_u/ HP-3ywAb=( zA|9,s+a3/ $i4qy&{#P` 3!^w<w~(Ra
-^;=Y4pE$X KW#HVuT7"j jH}:~#N3sc q!_}@:3Fpv [~.mHzYUM4 A@iNuL4]`P NfcR.9{qR~
]]'fv7U'i9 r7C{Reo^[# (ccRv*M4e> <7A#-'d{_a n$9ziJ|mm| mo]3kY/fzV 3(/%33;e,A
LU"$M`[3>j Nbxa<4v(KX tq9Kr@V-/< 7cjqU*dp;A v/TJJRWN7: ps%ea3jTik $+t%3E;7!U
T~\TzaP\9U X(}(f9]3t_ N3K3*%d)}7 4re[-!X,K' .q#99g?KqE 4"cAR]{azb }@[`A3F)ze
KK&~Me&_$4 )U4|mj&g\| f"=xn7"@uM <^xoY~?9?/ .C+4=|oFep F44T?`3A^] &44+:f=\Pa
`Xh4?J!gH7 }"cXT7H|pk KjtU3>"}zV 4UJR+%YY77 9Pq@@T\Ue~ #'o44~A%CJ kR':yV:h3/

Or 3 password 50 character long and so on:

$ pwgen -sBy 50 3
/{3>w<~hV>a4$C!%H!=^f&U\aMc,$y~Y!d+(K<$}x%V$~p'R|?
z7;[RAktU7y-p@*AK]\*c#;4CuW|hF+iv"-FR%nU'^_p)aH~i]
=T)C{^hK(dp_=ci*ft7~7TT|nVid-^?](aN%Yy[s&{d7u#<Pvk

Please check the man page for pwgen for all the possible options.

This tool is so simple and efficient. I use it in every OS, with Windows and WSL is straightforward to use it (and simple to get it with any package manager)within the cmd prompt or from powershell adding just WSL before pwgen command to have the same result. With MacOS and home-brew is just as simple to install it.

When do I need to generate password?

This question is interesting. A password should expire (frequently) and should be unique (as definition of secret and security). For this reason creating a new password and having the ability to generate it must simple and fast as possible.
There are many password manager tools available and most of them will provide or suggest a randomly generated password for you. Also Google Chrome can generate a password with a right-click on the password field, mozilla firefox has many add-ins or plugins with a similar feature.

In almost every company the most popular use for generating random password is more likely a part of an on-boarding script for generate AD Users or an automated password reset, when is required to generate a random password and not to depend from third-party modules if possible or desirable.

I prefer to re-use code as especially aiming for a robust solution and focus my efforts on solving problems and write code that is not already part of a library/api or module, but to create a lightweight password generator are just few lines of code.

My PowerShell simplified version of pwgen

This powershell script generates a password.  It’s a simple function that has an integer parameter for the password length (between 8 and 32 characters), generates a random choice from any available common ascii code and validate the result with a Regular Expression , just to check if the password is strong enough to meet the common password complexity requirements of Active Directory.

# Paolo Frigo, 2018 
# https://www.scriptinglibrary.com

Function New-RandomPassword{
    Param(
        [ValidateRange(8, 32)]
        [int] $Length = 16
    )   
    $AsciiCharsList = @()   
    foreach ($a in (33..126)){
        $AsciiCharsList += , [char][byte]$a 
    }
    #RegEx for checking general AD Complex passwords
    $RegEx = "(?=^.{8,32}$)((?=.*\d)(?=.*[A-Z])(?=.*[a-z])|(?=.*\d)(?=.*[^A-Za-z0-9])(?=.*[a-z])|(?=.*[^A-Za-z0-9])(?=.*[A-Z])(?=.*[a-z])|(?=.*\d)(?=.*[A-Z])(?=.*[^A-Za-z0-9]))^.*"

    do {
        $Password = ""
        $loops = 1..$Length
        Foreach ($loop in $loops) {
            $Password += $AsciiCharsList | Get-Random
        }
    }
    until ($Password -match $RegEx )   
    return $Password   
}

# This example just print a random password
# Write-Output "Generate Random Password: $(New-RandomPassword(10))"

And if I want a result like formatted like pwgen I just need 2 nested for loops:

#Generate a passwords similar to pwgen"
for ($i = 0; $i -lt (12); $i++) {
    $line = ""
    for ($j = 0; $j -lt (5); $j++) {
        $line += "$(New-RandomPassword(10)) "
    }
    Write-Output $line
}

This is the end result, very similar indeed.

PS /> ./New-RandomPassword.ps1
@m#w"$K9jX ,<5,*'Q{hp ^3Td&t,e$I C&wNkE.}1{ DT!%+jMom4
AT1M*LF4!/ h]KiooN9$0 ^5tM@E+qxB FG+Rut$6\P i0Z-n#xYO'
U]^xu9+b'` ~(l?z71'&x gV20RQkh%, j^di<I4#J& 6sVMx`%Dmy
G@oKZ1-d_g +Ea5iw1Qf% 67dNU$7]Rq =#s{(X8'VK :6@f<60!(Y
*^QBT51&m? P,5FH%3&um (|~K4]!:bP &8DFgc"%f& z5&iGsH:nx
HX*!5rW!DW STECR2^5%* VM9'(,Wx1! mgrI2\-v@i x32$6.$331
%p1:~Guf2+ :%n=tw^+a7 3Ks73J@s|* N5[+}&ndNR >"*GroBR3B
`Jkm\jk3#$ *56Hw[;(YB ,O|$bM0k5s %`5W@oyNma \X}+s6"yY#
[\<Jf!94[9 x~i-,$M3/@ &]MVC][N2H XAH},5x1#{ +n^3g'juMU
2?9$:a;{cp o_pvN6hd$A $\6V50ew`: kb5?&el?c7 k"$HhwTM-9
;L1DH%s-t? }?h~1L@uoo 79v!wp]ZMJ C;c*O<0S+B e8^kRnT0-g
bZ[,}q[\1# h4&;>^0Z>< #]5^rztu8i R_}^{Wat3S |LQENG&jH4

As usual, you can find this on my github repository.

Pester

Adding several unit tests for an automated script is key for a robust application, in this case the script is simple, but the results is really interesting:

Invoke-Pester .\New-RandomPassword.Tests.ps1 -CodeCoverage .\New-RandomPassword.ps1





Describing New-RandomPassword
 [+] Should generate a String 133ms
 [+] Should throw an exeption if the password lenght (0) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (1) is out of the accepted range (8-32) 21ms
 [+] Should throw an exeption if the password lenght (33) is out of the accepted range (8-32) 19ms
 [+] Should throw an exeption if the password lenght (34) is out of the accepted range (8-32) 21ms
 [+] Should throw an exeption if the password lenght (35) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (36) is out of the accepted range (8-32) 17ms
 [+] Should throw an exeption if the password lenght (37) is out of the accepted range (8-32) 15ms
 [+] Should throw an exeption if the password lenght (38) is out of the accepted range (8-32) 15ms
 [+] Should throw an exeption if the password lenght (39) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (40) is out of the accepted range (8-32) 19ms
 [+] Should throw an exeption if the password lenght (41) is out of the accepted range (8-32) 14ms
 [+] Should throw an exeption if the password lenght (42) is out of the accepted range (8-32) 24ms
 [+] Should throw an exeption if the password lenght (43) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (44) is out of the accepted range (8-32) 21ms
 [+] Should throw an exeption if the password lenght (45) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (46) is out of the accepted range (8-32) 20ms
 [+] Should throw an exeption if the password lenght (47) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (48) is out of the accepted range (8-32) 15ms
 [+] Should throw an exeption if the password lenght (49) is out of the accepted range (8-32) 17ms
 [+] Should throw an exeption if the password lenght (50) is out of the accepted range (8-32) 21ms
 [+] Should throw an exeption if the password lenght (51) is out of the accepted range (8-32) 20ms
 [+] Should throw an exeption if the password lenght (52) is out of the accepted range (8-32) 27ms
 [+] Should throw an exeption if the password lenght (53) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (54) is out of the accepted range (8-32) 22ms
 [+] Should throw an exeption if the password lenght (55) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (56) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (57) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (58) is out of the accepted range (8-32) 19ms
 [+] Should throw an exeption if the password lenght (59) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (60) is out of the accepted range (8-32) 19ms
 [+] Should throw an exeption if the password lenght (61) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (62) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (63) is out of the accepted range (8-32) 17ms
 [+] Should throw an exeption if the password lenght (64) is out of the accepted range (8-32) 17ms
 [+] Should throw an exeption if the password lenght (65) is out of the accepted range (8-32) 23ms
 [+] Should throw an exeption if the password lenght (66) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (67) is out of the accepted range (8-32) 19ms
 [+] Should throw an exeption if the password lenght (68) is out of the accepted range (8-32) 15ms
 [+] Should throw an exeption if the password lenght (69) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (70) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (71) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (72) is out of the accepted range (8-32) 17ms
 [+] Should throw an exeption if the password lenght (73) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (74) is out of the accepted range (8-32) 17ms
 [+] Should throw an exeption if the password lenght (75) is out of the accepted range (8-32) 14ms
 [+] Should throw an exeption if the password lenght (76) is out of the accepted range (8-32) 20ms
 [+] Should throw an exeption if the password lenght (77) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (78) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (79) is out of the accepted range (8-32) 20ms
 [+] Should throw an exeption if the password lenght (80) is out of the accepted range (8-32) 21ms
 [+] Should throw an exeption if the password lenght (81) is out of the accepted range (8-32) 15ms
 [+] Should throw an exeption if the password lenght (82) is out of the accepted range (8-32) 19ms
 [+] Should throw an exeption if the password lenght (83) is out of the accepted range (8-32) 15ms
 [+] Should throw an exeption if the password lenght (84) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (85) is out of the accepted range (8-32) 14ms
 [+] Should throw an exeption if the password lenght (86) is out of the accepted range (8-32) 20ms
 [+] Should throw an exeption if the password lenght (87) is out of the accepted range (8-32) 14ms
 [+] Should throw an exeption if the password lenght (88) is out of the accepted range (8-32) 22ms
 [+] Should throw an exeption if the password lenght (89) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (90) is out of the accepted range (8-32) 19ms
 [+] Should throw an exeption if the password lenght (91) is out of the accepted range (8-32) 17ms
 [+] Should throw an exeption if the password lenght (92) is out of the accepted range (8-32) 17ms
 [+] Should throw an exeption if the password lenght (93) is out of the accepted range (8-32) 21ms
 [+] Should throw an exeption if the password lenght (94) is out of the accepted range (8-32) 13ms
 [+] Should throw an exeption if the password lenght (95) is out of the accepted range (8-32) 15ms
 [+] Should throw an exeption if the password lenght (96) is out of the accepted range (8-32) 19ms
 [+] Should throw an exeption if the password lenght (97) is out of the accepted range (8-32) 16ms
 [+] Should throw an exeption if the password lenght (98) is out of the accepted range (8-32) 18ms
 [+] Should throw an exeption if the password lenght (99) is out of the accepted range (8-32) 21ms
 [+] Should throw an exeption if the password lenght (100) is out of the accepted range (8-32) 15ms
 [+] Should generate a password 8 character long 27ms
 [+] Should generate a password 9 character long 26ms
 [+] Should generate a password 10 character long 24ms
 [+] Should generate a password 11 character long 29ms
 [+] Should generate a password 12 character long 25ms
 [+] Should generate a password 13 character long 25ms
 [+] Should generate a password 14 character long 28ms
 [+] Should generate a password 15 character long 37ms
 [+] Should generate a password 16 character long 24ms
 [+] Should generate a password 17 character long 33ms
 [+] Should generate a password 18 character long 31ms
 [+] Should generate a password 19 character long 30ms
 [+] Should generate a password 20 character long 33ms
 [+] Should generate a password 21 character long 33ms
 [+] Should generate a password 22 character long 34ms
 [+] Should generate a password 23 character long 31ms
 [+] Should generate a password 24 character long 29ms
 [+] Should generate a password 25 character long 55ms
 [+] Should generate a password 26 character long 30ms
 [+] Should generate a password 27 character long 31ms
 [+] Should generate a password 28 character long 33ms
 [+] Should generate a password 29 character long 33ms
 [+] Should generate a password 30 character long 37ms
 [+] Should generate a password 31 character long 37ms
 [+] Should generate a password 32 character long 33ms
 [+] Should generate a password complex enough for AD (1/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (2/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (3/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (4/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (5/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (6/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (7/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (8/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (9/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (10/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (11/300 attempt) 39ms
 [+] Should generate a password complex enough for AD (12/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (13/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (14/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (15/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (16/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (17/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (18/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (19/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (20/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (21/300 attempt) 39ms
 [+] Should generate a password complex enough for AD (22/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (23/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (24/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (25/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (26/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (27/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (28/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (29/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (30/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (31/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (32/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (33/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (34/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (35/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (36/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (37/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (38/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (39/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (40/300 attempt) 22ms
 [+] Should generate a password complex enough for AD (41/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (42/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (43/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (44/300 attempt) 41ms
 [+] Should generate a password complex enough for AD (45/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (46/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (47/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (48/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (49/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (50/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (51/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (52/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (53/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (54/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (55/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (56/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (57/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (58/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (59/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (60/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (61/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (62/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (63/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (64/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (65/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (66/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (67/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (68/300 attempt) 43ms
 [+] Should generate a password complex enough for AD (69/300 attempt) 22ms
 [+] Should generate a password complex enough for AD (70/300 attempt) 42ms
 [+] Should generate a password complex enough for AD (71/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (72/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (73/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (74/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (75/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (76/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (77/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (78/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (79/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (80/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (81/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (82/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (83/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (84/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (85/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (86/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (87/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (88/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (89/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (90/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (91/300 attempt) 21ms
 [+] Should generate a password complex enough for AD (92/300 attempt) 46ms
 [+] Should generate a password complex enough for AD (93/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (94/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (95/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (96/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (97/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (98/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (99/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (100/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (101/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (102/300 attempt) 43ms
 [+] Should generate a password complex enough for AD (103/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (104/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (105/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (106/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (107/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (108/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (109/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (110/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (111/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (112/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (113/300 attempt) 42ms
 [+] Should generate a password complex enough for AD (114/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (115/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (116/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (117/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (118/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (119/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (120/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (121/300 attempt) 45ms
 [+] Should generate a password complex enough for AD (122/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (123/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (124/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (125/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (126/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (127/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (128/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (129/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (130/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (131/300 attempt) 42ms
 [+] Should generate a password complex enough for AD (132/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (133/300 attempt) 38ms
 [+] Should generate a password complex enough for AD (134/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (135/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (136/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (137/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (138/300 attempt) 22ms
 [+] Should generate a password complex enough for AD (139/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (140/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (141/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (142/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (143/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (144/300 attempt) 39ms
 [+] Should generate a password complex enough for AD (145/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (146/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (147/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (148/300 attempt) 21ms
 [+] Should generate a password complex enough for AD (149/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (150/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (151/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (152/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (153/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (154/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (155/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (156/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (157/300 attempt) 43ms
 [+] Should generate a password complex enough for AD (158/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (159/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (160/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (161/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (162/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (163/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (164/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (165/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (166/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (167/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (168/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (169/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (170/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (171/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (172/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (173/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (174/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (175/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (176/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (177/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (178/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (179/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (180/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (181/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (182/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (183/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (184/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (185/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (186/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (187/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (188/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (189/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (190/300 attempt) 43ms
 [+] Should generate a password complex enough for AD (191/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (192/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (193/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (194/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (195/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (196/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (197/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (198/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (199/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (200/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (201/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (202/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (203/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (204/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (205/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (206/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (207/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (208/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (209/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (210/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (211/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (212/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (213/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (214/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (215/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (216/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (217/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (218/300 attempt) 22ms
 [+] Should generate a password complex enough for AD (219/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (220/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (221/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (222/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (223/300 attempt) 21ms
 [+] Should generate a password complex enough for AD (224/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (225/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (226/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (227/300 attempt) 39ms
 [+] Should generate a password complex enough for AD (228/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (229/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (230/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (231/300 attempt) 38ms
 [+] Should generate a password complex enough for AD (232/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (233/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (234/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (235/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (236/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (237/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (238/300 attempt) 38ms
 [+] Should generate a password complex enough for AD (239/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (240/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (241/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (242/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (243/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (244/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (245/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (246/300 attempt) 43ms
 [+] Should generate a password complex enough for AD (247/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (248/300 attempt) 42ms
 [+] Should generate a password complex enough for AD (249/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (250/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (251/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (252/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (253/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (254/300 attempt) 40ms
 [+] Should generate a password complex enough for AD (255/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (256/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (257/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (258/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (259/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (260/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (261/300 attempt) 39ms
 [+] Should generate a password complex enough for AD (262/300 attempt) 25ms
 [+] Should generate a password complex enough for AD (263/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (264/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (265/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (266/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (267/300 attempt) 27ms
 [+] Should generate a password complex enough for AD (268/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (269/300 attempt) 30ms
 [+] Should generate a password complex enough for AD (270/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (271/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (272/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (273/300 attempt) 22ms
 [+] Should generate a password complex enough for AD (274/300 attempt) 38ms
 [+] Should generate a password complex enough for AD (275/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (276/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (277/300 attempt) 28ms
 [+] Should generate a password complex enough for AD (278/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (279/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (280/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (281/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (282/300 attempt) 32ms
 [+] Should generate a password complex enough for AD (283/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (284/300 attempt) 26ms
 [+] Should generate a password complex enough for AD (285/300 attempt) 24ms
 [+] Should generate a password complex enough for AD (286/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (287/300 attempt) 34ms
 [+] Should generate a password complex enough for AD (288/300 attempt) 33ms
 [+] Should generate a password complex enough for AD (289/300 attempt) 22ms
 [+] Should generate a password complex enough for AD (290/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (291/300 attempt) 36ms
 [+] Should generate a password complex enough for AD (292/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (293/300 attempt) 23ms
 [+] Should generate a password complex enough for AD (294/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (295/300 attempt) 31ms
 [+] Should generate a password complex enough for AD (296/300 attempt) 37ms
 [+] Should generate a password complex enough for AD (297/300 attempt) 35ms
 [+] Should generate a password complex enough for AD (298/300 attempt) 29ms
 [+] Should generate a password complex enough for AD (299/300 attempt) 22ms
 [+] Should generate a password complex enough for AD (300/300 attempt) 30ms
Tests completed in 11.48s
Passed: 396 Failed: 0 Skipped: 0 Pending: 0 Inconclusive: 0

Code coverage report:
Covered 100.00% of 11 analyzed commands in 1 file.

Code coverage of 100% and hundreds of tests passed make me feel confident that this function is resilient and in case a new issue will be found, I can simply add a specific test to catch/prevent it from happening again in case feature changes are modifying the behaviour of my code.

And this is the Pester script used for unit testing:

# Paolo Frigo, 2018 
# https://www.scriptinglibrary.com

. .\New-RandomPassword.ps1 

Describe "New-RandomPassword" -Tags "Unit Tests" {
    it "Should generate a String" {
        (New-RandomPassword).GetType().Name | Should BeExactly "String"
    }

    #Pick a password Length between 0 and 7 and 33 and 100 characters  
    $n = 0..1 + 33..100 
    foreach ($length in $n){
        it "Should throw an exeption if the password Length ($length) is out of the accepted range (8-32)"    {
            {New-RandomPassword -Length 5} | Should throw
        }
    }
    #Pick a password Length between 8 and 32 characters   
    $n = 8..32 
    foreach ($length in $n){
        It "Should generate a password $length character long" {
            (New-RandomPassword($length)).length | Should BeExactly "$length"     
        }   
    }  
    #Test/Generate 300 passwords
    foreach ($attempt in (1..300)){
        It "Should generate a password complex enough for AD ($attempt/300 attempt)"{
            $n = 8..32 | Get-Random 
            $RegEx = "(?=^.{8,32}$)((?=.*\d)(?=.*[A-Z])(?=.*[a-z])|(?=.*\d)(?=.*[^A-Za-z0-9])(?=.*[a-z])|(?=.*[^A-Za-z0-9])(?=.*[A-Z])(?=.*[a-z])|(?=.*\d)(?=.*[A-Z])(?=.*[^A-Za-z0-9]))^.*"
            (New-RandomPassword($n)) -match $RegEx
        }
    }    
}

 

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