The installation works pretty much flawlessly. However, as a precaution I answer all installation questions in the negative to avoid giving the program extra work.
On first run the program crashes twice. Just re-open and go on.
What does not
Text recognition only runs with other programs running in wine. This is correct functionality, not a bug.
For best results use Notepad or the included DragonPad.
What was not tested
The program has some settings that are not essential to its core function. These were not tested.
The program is a 32-bit program with a 64-bit wrapper. For best results install in a 32-bit wine prefix. Use pulseaudio. set winecfg to Vista and pulseaudio input.
|Operating system||Test date||Wine version||Installs?||Runs?||Used|
|Show||Debian GNU/Linux 9.x "Stretch" x86_64||Oct 12 2018||3.0.2||Yes||Yes||Yes||Silver||Susan Cragin|
|Current||Ubuntu 14.10 "Utopic" i386 (+ variants like Kubuntu)||May 23 2014||1.7.19||Yes||Yes||Silver||Susan Cragin|
|Show||Linux Mint 17 "Qiana" x86_64||Jul 29 2014||1.6.2||Yes||No||Garbage||Jay Starkman|
|Show||Ubuntu 13.10 "Saucy" amd64 (+ variants like Kubuntu)||Nov 20 2013||1.7.4||Yes||Yes||Silver||Susan Cragin|
|Show||Ubuntu 13.04 "Raring" amd64 (+ variants like Kubuntu)||Apr 12 2013||1.5.27||Yes||Yes||Silver||Susan Cragin|
As of wine 3.6(staging), and possibly earlier, NatSpeak 12.5 installs and runs under a 64-bit wineprefix.
I installed it on 28-Apr-2018 and the only special concession I made to the wineprefix was to uninstall mono. Installing dotnet 40 with winetricks also works. Both optiions tell the program that an inadequate version of net is installed, and prompt the program to install its own.
After the installation, it says you have to reboot. I kill wineserver at the terminal and then start the installation process over. It does, bypassing the net installation.
All in all, NatSpeak works wonderfully now, and version 12.5 is very accurate and the latest low-end (and cheap) version to work well.
Dragon NaturallySpeaking 12.5 is actually not obsolete, since many people still use it, and it was the last Dragon Naturally Speaking to run well on wine.
Versions 13 and 15, both newer, cannot be installed.
12.5 can be installed. However, it no longer runs. A bug crops up after you have created a user profile, and before you first use it.
So there is no working version of Dragon Naturally Speaking right now.
I last tested 12.5 with wine-4.3 (Staging) and it does not run.