OK, no punctuation, no empty words, etc.... My lowest bid: 74 chars

ClassMethod Order(s)
{
	f  s p=$p(s," ",$i(i)),w=$tr(p,1/17),$p(z," ",$tr(p,w))=w ret:p=w $g(z)
}

By the way, the following three variants all have the same size of 74

	f  s p=$p(s," ",$i(i)),w=$tr(p,1/17),$p(z," ",$tr(p,w))=w ret:p=w $g(z)
	f{s p=$p(s," ",$i(i)),w=$tr(p,1/17),$p(z," ",$tr(p,w))=w ret:p=w $g(z)}
1	s p=$p(s," ",$i(i)),w=$tr(p,1/17),$p(z," ",$tr(p,w))=w q:p=w $g(z) g 1	

A small complaint:
- possible word delimiters weren't specified (space, tab, etc.)
- no specification about punctuation marks (allowed or disallowed)
- no specification about empty words (allowed or disallowed) and how to handle them, if allowed

So my question is, are the following examples legal or not:

"O2K. I'1m" --> "I'm OK."
"spac4es are2    1There     ma3ny" --> "There are many spaces."

Putting all in one line saves one byte

ClassMethod Order(s As %String) As %String
{
	s d=" ",z="" f i=1:1:$l(s,d){s b=$p(s,d,i),c=$zstrip(b,"*n"),$p(z,d,$tr(b,c))=c} q z
}

Changing $zstrip() to a $tr() saves one more byte

ClassMethod Order(s As %String) As %String
{
	s d=" ",z="" f i=1:1:$l(s,d){s b=$p(s,d,i),c=$tr(b,1E20/17),$p(z,d,$tr(b,c))=c} q z
}

So I end up with 86 bytes

One of the possible solutions

/// You can change the s:b]"" to an comma if there is always exact one space between the words
/// and remove the ,1) from $lts() if all word are numbered from 1..N with no number missing
ClassMethod WordOrder(s)
{
    s z="" f i=1:1:$l(s," ") s b=$p(s," ",i) s:b]"" $li(z,$zstrip(b,"*ap"))=$zstrip(b,"*n")
    q $lts(z," ",1)
}

This is a working solution and maybe not the shortest

You can it enter via terminal, no question about, but it's a little bit cumbersome

// create the class
s cls=##class(%Dictionary.ClassDefinition).%New()
s cls.ProcedureBlock=1
s cls.Super="%RegisteredObject"
s cls.Name="ObjectScript.RightTriangle"

// add one method
s mth=##class(%Dictionary.MethodDefinition).%New()
s mth.Name="Main"
s mth.Description="Compute area and hypotenuse of a right triangle"
d mth.Implementation.WriteLine($c(9)_"write !,""Compute the area and hypotenuse of a right triangle"",")
d mth.Implementation.Write($c(9,9)_"!,""given the lengths of its two sides.""")
d cls.Methods.Insert(mth)

// add one more method
s mth=##class(%Dictionary.MethodDefinition).%New()
s mth.Name="Area",mth.Description="Area, computed from sides 'a' and 'b'"
s mth.FormalSpec="a,b"
d mth.Implementation.WriteLine($c(9)_"quit a*b/2")
d cls.Methods.Insert(mth)

// save the class (it's NOT compiled!)
w cls.%Save()

As you may see, creating a class via an IDE is simpler... but yes, in an emergency case you can do it also via a console access

First, ##class(%PopulateUtils).StringMin(16,16)    generates random printable chars for testing (as replacement for user input) and is not ment to be used to generate cryptographic random chars. If you need cryptographic random chars, use $system.Encryption.GenCryptRand(length). This is just a hint and is not a reason for your current problem.

Second, despite my very limited C# experience, there is one thing in your code, I do not understand. If the initial vector (IV) is used, then it should be used (for enryption and decryption) the same IV on both sides, but you create an IV on Cache side (with the populate utils) and an other one on the C# side: byte[] IV = new byte[16]; (new Random()).NextBytes(IV);

That your decryption can't work.

To have a successful comunication, agree with the other party on
- a passphrase (the key), padding is done inside the encoding function 
- an IV (or left it empty on both sides)
- and on how the data will be sent:  either as the encoded (binary) data or as a readable (base64) data.ISC's implementation of AESCBCEncrtypt/Decrypt works well. One of my application uses it to communicate with an Windows application written in Delphi, without any problem since more the 15 years (we do not use the IV). So your problem will be some kind of a home-made problem:
- not using the same keys on both sides
- applying some kind of transformation (utf-8, base64, etc.)
- something suchlike

One of the problems could be the Bas64 encoding. This function inserts after each 76th byte a CRLF which possibly confuses the other party. Try with 

Set EncryptedBase64=$SYSTEM.Encryption.Base64Encode(encrypted, 1)

The parameter 1 says, do not insert CRLFs. Also, the text you encrypt must be an ANSI (8bit) text. If you are on a unicode system, you should call

Set encrypted=$SYSTEM.Encryption.AESCBCEncrypt($zcvt(text,"O","UTF8"),key,iv)

I understand your answer (#2) the way as this is a one time job. The simplest and quickest way to do this is:

- disable all indices (comment them out),
- compile the class or classes
- do the bulk insert
- enable all indices (by removing comment markers)
- compile the class or classes
- rebuild the indices

Class My.Class
{
    /*  disable all indices
    index1 someindex1 on someprop1;
    index2 someindex2 on someprop2;
    */
}

I do not use Ensemble, but I would try using the JSON-Adaptor, something like this

Class MessageB Extends (Ens.Request, %JSON.Adaptor)
{
   Property ClientId As %String(MAXLEN = "");
   Property message As %Stream.TmpBinary;
}

For example

s r=##class(MessageB).%New()
s r.ClientId=12345
d r.message.Write("part1")
d r.message.Write("part2")
w r.%JSONExportToStream(.s)
d s.Rewind()
w s.Read(s.Size) --> {"ClientId":"12345","message":"cGFydDFwYXJ0Mg=="}

Your solution is nearly perfect, here my quick (untested) version.


ClassMethod Encode()
{
	// You read N bytes (which MUST be divisible by 3) and write N*4/3 encoded bytes
	// 3 * 8190 = 24570; 24570 * 4 / 3 = 32760;  32760 < 32768; to avoid (slow) long strings
	set CHUNK=24570
	set NOCR=1	// don't insert CRLF after each 72 written bytes
	set encodedData=##class(%Stream.TmpBinary).%New() // adapt this to your needs: %Stream.Whatever...
	
	set request=##class(%Net.HttpRequest).%New()
	set request.Server="..."
    do request.Get("/...")
    
    if request.HttpResponse.StatusCode = 200 {
    	while 'request.HttpResponse.Data.AtEnd {
	    	do encodedData.Write($system.Encryption.Base64Encode(request.HttpResponse.Data.Read(CHUNK),1))
		}
	}
    QUIT encodedData
    
    // as an alternative, you could return a string or a streamobject
    set YOURMAXSTRING = 32767 // or 3641144
    if encodedData.Size <= YOURMAXSTRING {
	    do encodedData.Rewind()
	    quit encodedData.Read(encodedData.Size)
    } else { quit encodedData }
}