Converting some Freehand files to editable illustrator PDF’s

In the hopes that this description of problems and workarounds will help someone out there somewhere.
Posted provisionally on 2026-01-28 !CHECK! – needs to be confirmed

Problems addressed:
#1 with some embedded images in a Freehand drawing (in my case: one bit Tiffs, scaled and made transparent in Freehand), image changes size and location slightly after opening the Freehand file in Adobe Illustrator. Exporting as EPS preserves scale and location of images better, but text is no longer editable – workaround below
#2 textbox not showing all text (shows a red plus ‘+’ symbol at smaller scale views !CHECK! )
#3 spot colours converted to process on import (!CHECK! is this also the case when opening directly)

ai = Adobe Illustrator
FH = Freehand

Background and details:
I’m converting older Freehand files to editable Adobe illustrator PDF’s. These are intended for publication, but may require some minor edits in the future. The original files are Freehand 9 format, and roughly twenty years old. Note I have installed Freehand 9 on my Windows 10 machine, and it is working very well. I’m unable to create a successful PDF directly from the FH file (even if I could, it would be no longer editable in illustrator). The files contain very large embedded TIFF files and will be printed/published at up to a metre in length (as pull-outs in an academic volume).

As usually the case when trying to convert from one file format to another, it’s been a bit of a nightmare. I’m using Adobe illustrator CS4 on a Windows 10 machine. From versions CS3 to CS5, Adobe offered the option to open Freehand files directly within illustrator. I have read that later versions of illustrator no longer have this ability, but it can be added using a paid plug-in from Tensai AI Plugins.

Description of the Freehand files content:

embedded high resolution one-bit TIFF files (one-bit tiffs are black/white images). These are made transparent (i.e. just the black shows, no white)
colour highlighting added on a lower layer (filled vector)
vector drawing
text

Problem #1 registration/alignment of elements incorrect:
My main problem is that the embedded tiff files change slightly in size when the FH file is opened in ai, so the highlighting is no longer correctly aligned/registered. The tiff files are large and I was unable to tweak them to align correctly. Small areas are highlighted, spread out over a large file — I was also unable to get the highlighting to align well by simply moving the highlighting vectors (or it was too labour intensive for multiple files with multiple highlighting).
!CHECK!

1.2 If I export the Freehand file as an EPS file, and import this into ai, the alignment is now correct, but the text gets converted to paths and is no longer editable. So, at the moment, my solution starts by creating two versions of the FH file: first with no text, second with only text.

1.3 I export the text-free file as EPS — this then imports correctly in ai
Now, open the Freehand file with just the text – open it directly in ai. Select and copy all the text and paste it in a new layer in the imported EPS. This text needs to get lined up correctly (compare with the original). See next:

Problem #2 text displaying incorrectly:
On opening a FH file in ai, some textboxes will have a red “+” plus-symbol and their content will not be fully visible. For some reason an extra space character is occasionally added (from memory: I think at the end !CHECK! ). The textbox comes through with a fixed size and no longer shows all the text. You will have to go into the box and edit/remove the extra space. Text should now show properly.

Problem #3 spot > process:
This mainly a warning / minor: spot colours are converted to process. These have to be converted to spot within illustrator.