The problem seems to be resolved. Thanks to everyone, especially Hans, Taco and 
Wolfgang for the fast fix (offlist)!

After updating to

ConTeXt  ver: 2020.01.30 14:13 MKIV beta  fmt: 2020.4.26

Helvetica Neue works with:
==========================

\starttypescript [sans] [helvet]
   \setups[font:fallback:sans]
   \definefontsynonym [Sans]           [file:Helvetica Neue.ttc(Helvetica 
Neue)]     [features=default]
   \definefontsynonym [SansBold]       [file:Helvetica Neue.ttc(Helvetica Neue 
Bold)]       [features=default]
   \definefontsynonym [SansItalic]     [file:Helvetica Neue.ttc(Helvetica Neue 
Italic)]      [features=default]
   \definefontsynonym [SansBoldItalic] [file:Helvetica Neue.ttc(Helvetica Neue 
Bold Italic)] [features=default]
\stoptypescript

\definetypeface [helvet] [ss] [sans] [helvet] [default] 

\setupbodyfont [helvet, 12pt]

Optima works with:
==================

\starttypescript [sans] [optima]
  \setups[font:fallback:sans]
  \definefontsynonym [Sans]           [file:Optima.ttc(Optima Regular)]     
[features=default]
  \definefontsynonym [SansBold]       [file:Optima.ttc(Optima Bold)]       
[features=default]
  \definefontsynonym [SansItalic]     [file:Optima.ttc(Optima Italic)]      
[features=default]
  \definefontsynonym [SansBoldItalic] [file:Optima.ttc(Optima Bold Italic)] 
[features=default]
\stoptypescript

\definetypeface [optima] [ss] [sans] [optima] [default]

\setupbodyfont [optima]

\starttext
\tf Upright,
\bf Bold,
\it Italic,
\bi Bolditalic
\stoptext

Note 1: mtxrun --script fonts --list --all --pattern=helvetica etc. might still 
not display all variants correctly in the first place.

Note 2: There are predefined typescripts for Mac OS in ConTeXt 
(type-imp-osx.mkiv) but the file needs a update/cleanup.

> On 24 Apr 2020, at 12:14, Benjamin Buchmuller <benjamin.buchmul...@gmail.com> 
> wrote:
> 
> Hi Hraban,
> 
> Thanks for the hint (and the proper fontfamily setup), I have forced reload 
> ten times now from various accounts; the issue persists unfortunately. 
> 
> This might confirm Taco‘s notion that there is some bug lmtx. I’m running 
> macOS Catalina too, but as it worked with the standalone of Dec/Jan three 
> days ago, I suspect it is not because of a new feature in the OS, but rather 
> an old feature in mtxrun or elsewhere having disappeared. 
> 
>> On 24. Apr 2020, at 11:35, Henning Hraban Ramm <te...@fiee.net> wrote:
>> 
>> 
>> 
>>> Am 24.04.2020 um 11:13 schrieb Benjamin Buchmuller 
>>> <benjamin.buchmul...@gmail.com>:
>>> 
>>> Although this specific issue might have been solved meanwhile by the 
>>> helpful suggestions of Wolfang, Thomas and others, I would like to point 
>>> out that I have recently also encountered an odd behaviour of the mtxrun 
>>> fontloader in the standalone, in which not all typefaces are 
>>> available/properly identified.
>>> 
>>> (I’m sorry to hijack this thread if this is unrelated.)
>>> 
>>> Basically, when I load “Helvetica Neue”, I get instead of “regular/normal” 
>>> always “light/italic”.
>>> 
>>> I have switched to heros for the meantime, but potentially there is some 
>>> bug behind this. (My documents with the version from Dec/Jan worked fine.)
>>> 
>>> I recite my example from Wed:
>>> 
>>> ConTeXt  ver: 2020.01.30 14:13 MKIV beta  fmt: 2020.4.22 (LuaTeX 1.11.1)
>>> 
>>> and I’m running now into troubles with system font indexing:
>>> 
>>> mtxrun --script fonts --reload
>>> 
>>> locates fonts in macOS directories appropriately (*.afm fonts placed in 
>>> .../tex/texmf-fonts are not found, but at the moment I don’t care too 
>>> much), however it resolves only to a single font variant for *.ttc instead 
>>> of all variants:
>>> 
>>> mtxrun --script fonts --list --all --pattern=helvetica
>>> 
>>> helvetica                         helvetica                    
>>> helveticalightoblique         /System/Library/Fonts/Helvetica.ttc           
>>>          6
>>> helveticalightoblique             helvetica                    
>>> helveticalightoblique         /System/Library/Fonts/Helvetica.ttc           
>>>          6
>>> helveticaneuedeskinterfaceheavy   helveticaneuedeskinterface   
>>> helveticaneuedeskinterfaceheavy   
>>> /System/Library/Fonts/HelveticaNeueDeskInterface.ttc   10
>>> helveticaneuethinitalic           helveticaneue                
>>> helveticaneuethinitalic       /System/Library/Fonts/HelveticaNeue.ttc       
>>>          14
>> 
>> If the subfont is not listed, ConTeXt/mtxrun couldn’t find it and won’t find 
>> it regardless of your setup.
>> 
>> Try
>> mtxrun --script fonts --reload --force
>> maybe even twice or thrice and check again.
>> (Unfortunately this is not reliable.)
>> 
>> I get the full list:
>> 
>> identifier                               familyname                   
>> fontname                                   filename                          
>>                      subfont   instances
>> 
>> helvetica                                helvetica                    
>> helvetica                                  
>> /System/Library/Fonts/Helvetica.ttc                    1
>> helveticaneueblack                       helveticaneue                
>> helveticaneuecondensedblack                
>> /System/Library/Fonts/HelveticaNeue.ttc                10
>> helveticaneuedeskinterfaceextrabold      helveticaneuedeskinterface   
>> helveticaneuedeskinterfaceheavy            
>> /System/Library/Fonts/HelveticaNeueDeskInterface.ttc   10
>> helveticaneuedeskinterfaceextralight     helveticaneuedeskinterface   
>> helveticaneuedeskinterfacethin             
>> /System/Library/Fonts/HelveticaNeueDeskInterface.ttc   8
>> helveticaneuedeskinterfacemedium         helveticaneuedeskinterface   
>> helveticaneuedeskinterfacemediump4         
>> /System/Library/Fonts/HelveticaNeueDeskInterface.ttc   5
>> helveticaneuedeskinterfacemediumitalic   helveticaneuedeskinterface   
>> helveticaneuedeskinterfacemediumitalicp4   
>> /System/Library/Fonts/HelveticaNeueDeskInterface.ttc   6
>> helveticaneuedeskinterfacenormal         helveticaneuedeskinterface   
>> helveticaneuedeskinterfaceregular          
>> /System/Library/Fonts/HelveticaNeueDeskInterface.ttc   1
>> helveticaneueextralight                  helveticaneue                
>> helveticaneuethin                          
>> /System/Library/Fonts/HelveticaNeue.ttc                13
>> helveticaneuenormal                      helveticaneue                
>> helveticaneue                              
>> /System/Library/Fonts/HelveticaNeue.ttc                1
>> helveticaneueregular                     helveticaneue                
>> helveticaneue                              
>> /System/Library/Fonts/HelveticaNeue.ttc                1
>> helveticanormal                          helvetica                    
>> helvetica                                  
>> /System/Library/Fonts/Helvetica.ttc                    1
>> helveticaregular                         helvetica                    
>> helvetica                                  
>> /System/Library/Fonts/Helvetica.ttc                    1
>> 
>> 
>> 
>>> As a consequence, when I run
>>> 
>>> \definefontfamily[mainface][ss][Helvetica Neue]
>>> \setupbodyfont[mainface, 12pt, sans]
>>> 
>>> I get the light oblique variant instead of the regular one. I have tried to 
>>> fix this via a 
>>> 
>>> \definefontfamily[mainface][ss][Helvetica Neue][tf=style:normal]
>> 
>> tf=helveticaregular
>> should work.
>> 
>> 
>> Best, Hraban
>> 
>> 

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