I'm fiddling with compound paths and discovered something I cannot explain. It's baffling me.

  1. Create two text objects (e.g. A, B). Outline both, ungroup, release compound path and remove the bowl objects from the B and the triangle from A. You'll now have two closed paths that are the outline of the letter.

  2. Make a compound path using these outlines. The intersection is still filled in! See the image below.

  3. Now, repeat what you did but instead of removing the bowls and triangle, take a union of the released compound shape paths for each letter. This path makes a compound path with a copy of itself in the way you expect.

  4. There is no difference between the outline of the A with triangle removed and outline of the A that was formed by the union with the triangle. Both are closed paths. View > Document Info shows precisely the same information. Yet, they behave differently.

I'm totally stumped. Is this a bug?

Illustrator 27.0 MacOSX Monterey 12.4

enter image description here

3 Answers 3


No bug.

The A and B outline paths happen to have opposite directions. Change fill rule in Attributes panel from "use non-zero winding" to "use even-odd-rule"

  • Ok, wow. I had no idea that a closed path could have a direction. Thanks. Commented Nov 23, 2022 at 22:23

I've come across this problem before with compound paths, often for no obvious reason. However it has to do with the path direction of the compound paths. A bug or a feature, who knows!?

  1. Open up the Attributes panel Ctrl+F11, and you should be able to see what is going on.

  2. Select the left combined paths example, and note the Left path direction button is shown as selected

  3. Now select the right combined paths example, and note that no path direction is shown. I assume one of the paths here has a different path direction or neither are set for some reason, perhaps because of the Unite operation, and neither button is shown as selected

  4. The fix is simply to hit one of the path direction buttons.

enter image description here


I can replicate this easily. Does appear to be a bug perhaps.

Odd workaround....

  • Create Outlines
  • Ungroup
  • Release Compound Paths
  • Flatten Transparency or Expand
  • delete counters

...then it works as expected.

Now, there's zero transparency anywhere.... and there's nothing to expand... but for some reason those operations cause the paths to then operate as expected.

Also note I'm using CS6 at the moment, so if it's the same there.. well..

  • Yup, I can replicate your work around. Flattening transparency does something to these paths that makes them behave rationally again. As does expand. Commented Nov 22, 2022 at 21:26
  • 1
    Added expand above :) Once I saw Flatten Transparency worked, I quit looking :)
    – Scott
    Commented Nov 22, 2022 at 21:28

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