Square symbols don't always convert to check boxes
I'm using Adobe Acrobat XI. I used to use Adobe Acrobat X, and encountered the same problem.
I create some REALLY lengthy forms in Word. I apply a style with square bullets to text in Word to create a checkbox list. Then I convert the file to PDF, and then convert the PDF to a form. Every line has the same Word style with the same square symbol for its bullet, so there's nothing about the way I'm applying the formatting that's inconsistent.
I've learned from trial and error that square bullets only convert to checkboxes if the font is 10pt or larger. I've also learned that you have to apply a specific square symbol (I'm sorry - I don't have the ASCII code for it), or it won't work. I've tested numerous square symbols (Insert+Symbol in Word), and keep returning to my go-to square. This square even works when you insert it in the middle of a line.
Naturally, I never seem to encounter problems in one-page forms. But when I'm creating forms with hundreds or thousands of items on a checkbox list, only SOME of these square boxes convert to check boxes. I don't know why. Then I have to manually copy/paste the checkbox fields, move them into position, and give each one a unique name. It's crazy-making unnecessary work.
The font I use is Calibri because it's compact. I have to keep pages to a minimum, and larger, more spread-out fonts like Verdana create too many extra pages.
•I've tried breaking up the document into pages and converting each one separately, and most of the same checkboxes still don't convert in these smaller files.
•I've tried creating a new document and recreating the styles, then copy/pasting the content into the new file (I can't type it line-by-line to recreate it from scratch - the affected forms are far too long).
•I've tried increasing the font size to 11pt, but if it doesn't convert at 10pt, it won't convert at 11pt.
•I've changed the font, and checkboxes still don't convert.
•When I still had access to Adobe X, I tested converting the file in BOTH versions. There was some difference in which checkboxes didn't convert, but the problem was there too.
Please see the attached image.
The form field detection algorithm is not perfect, and only provides a good starting point.
You will require manual work to create fields that are not detected by Acrobat
As a workaround, you could try inserting “Square shape” instead of bullets.
Click Insert, click Shapes, select a shape, and then click and drag to draw the shape.
I hope this work for you.
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CreeLoPer27 commented
I had the same problem, from my limited testing I found out that the checkboxes are not getting recognized most of the times because the distance between the checkbox and the text is too large, I have highlighted the distances in your attached image to better show the distances that are ok (in green) and the distances that are too long (in red) and do not allow the checkbox to be recognised.
If you make that distance shorter they should get recognised (this should also be the same with square bullets as you said you are using)
I usually personally make forms with a giant table in word with invisible borders to format and place everything, I then make the bottom border of a cell visible (any color seems to work) to make that cell a writable text field (I know you can also put underscores but that approach gives less refined results from my experience), to make it a checkbox field I usually add the word checkbox in the table cell (you can follow this guide if you never used them: https://www.howtogeek.com/204036/how-to-add-check-boxes-to-word-documents/).
In both cases you need to make sure that the distance between the text describing the text field/checkbox and the text field/checkbox is as short as possible (as shown in the image).Another small trick if you are using the "table method" and you can't get the cell with the text describing the text field/checkbox and the text field/checkbox close enough to get detected is to hold "alt" while moving the line separating the 2 cells to get more fine control, if that is not enought either you can trick word into moving the line closer by adding an empty row below and then after that another empty row (2 rows down) where you add with the table drawing tool a line that is slightly closer than your original one, you can then move the original one and it should snap to the temporary one you created below without making the text describing the text field/checkbox go to a new line in its cell.
In conclusion I would say Adobe seriously needs to improve their automatic form detection/creation algortihms and make things like this invisible maximum detection distance configurable by the user, they should also add support for things like multiline text fields and others.