diff --git a/.changeset/beige-bats-switch.md b/.changeset/beige-bats-switch.md
new file mode 100644
index 000000000..1cd9a9e42
--- /dev/null
+++ b/.changeset/beige-bats-switch.md
@@ -0,0 +1,6 @@
+---
+"@primer/octicons": minor
+---
+
+- modifies tasklist icon proposed in https://github.com/github/primer/issues/746
+- adds a new checkbox icon using metaphor from previous tasklist metaphor
diff --git a/icons/checkbox-16.svg b/icons/checkbox-16.svg
new file mode 100644
index 000000000..d0245b85c
--- /dev/null
+++ b/icons/checkbox-16.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="16" height="16" viewBox="0 0 16 16"><path fill-rule="evenodd" d="M2.5 2.75a.25.25 0 01.25-.25h10.5a.25.25 0 01.25.25v10.5a.25.25 0 01-.25.25H2.75a.25.25 0 01-.25-.25V2.75zM2.75 1A1.75 1.75 0 001 2.75v10.5c0 .966.784 1.75 1.75 1.75h10.5A1.75 1.75 0 0015 13.25V2.75A1.75 1.75 0 0013.25 1H2.75zm9.03 5.28a.75.75 0 00-1.06-1.06L6.75 9.19 5.28 7.72a.75.75 0 00-1.06 1.06l2 2a.75.75 0 001.06 0l4.5-4.5z"/></svg>
\ No newline at end of file
diff --git a/icons/checkbox-24.svg b/icons/checkbox-24.svg
new file mode 100644
index 000000000..080fa7bc4
--- /dev/null
+++ b/icons/checkbox-24.svg
@@ -0,0 +1 @@
+<svg xmlns="http://www.w3.org/2000/svg" width="24" height="24" viewBox="0 0 24 24"><path d="M17.28 9.28a.75.75 0 00-1.06-1.06l-5.97 5.97-2.47-2.47a.75.75 0 00-1.06 1.06l3 3a.75.75 0 001.06 0l6.5-6.5z"/><path fill-rule="evenodd" d="M3.75 2A1.75 1.75 0 002 3.75v16.5c0 .966.784 1.75 1.75 1.75h16.5A1.75 1.75 0 0022 20.25V3.75A1.75 1.75 0 0020.25 2H3.75zM3.5 3.75a.25.25 0 01.25-.25h16.5a.25.25 0 01.25.25v16.5a.25.25 0 01-.25.25H3.75a.25.25 0 01-.25-.25V3.75z"/></svg>
\ No newline at end of file
diff --git a/icons/tasklist-16.svg b/icons/tasklist-16.svg
index d0245b85c..5aefce499 100644
--- a/icons/tasklist-16.svg
+++ b/icons/tasklist-16.svg
@@ -1 +1 @@
-<svg xmlns="http://www.w3.org/2000/svg" width="16" height="16" viewBox="0 0 16 16"><path fill-rule="evenodd" d="M2.5 2.75a.25.25 0 01.25-.25h10.5a.25.25 0 01.25.25v10.5a.25.25 0 01-.25.25H2.75a.25.25 0 01-.25-.25V2.75zM2.75 1A1.75 1.75 0 001 2.75v10.5c0 .966.784 1.75 1.75 1.75h10.5A1.75 1.75 0 0015 13.25V2.75A1.75 1.75 0 0013.25 1H2.75zm9.03 5.28a.75.75 0 00-1.06-1.06L6.75 9.19 5.28 7.72a.75.75 0 00-1.06 1.06l2 2a.75.75 0 001.06 0l4.5-4.5z"/></svg>
\ No newline at end of file
+<svg xmlns="http://www.w3.org/2000/svg" width="16" height="16" viewBox="0 0 16 16"><path fill-rule="evenodd" d="M2.5 3.5v3h3v-3h-3zM2 2a1 1 0 00-1 1v4a1 1 0 001 1h4a1 1 0 001-1V3a1 1 0 00-1-1H2zm4.655 8.595a.75.75 0 010 1.06L4.03 14.28a.75.75 0 01-1.06 0l-1.5-1.5a.75.75 0 111.06-1.06l.97.97 2.095-2.095a.75.75 0 011.06 0zM9.75 2.5a.75.75 0 000 1.5h5.5a.75.75 0 000-1.5h-5.5zm0 5a.75.75 0 000 1.5h5.5a.75.75 0 000-1.5h-5.5zm0 5a.75.75 0 000 1.5h5.5a.75.75 0 000-1.5h-5.5z"/></svg>
\ No newline at end of file
diff --git a/icons/tasklist-24.svg b/icons/tasklist-24.svg
index 080fa7bc4..744226971 100644
--- a/icons/tasklist-24.svg
+++ b/icons/tasklist-24.svg
@@ -1 +1 @@
-<svg xmlns="http://www.w3.org/2000/svg" width="24" height="24" viewBox="0 0 24 24"><path d="M17.28 9.28a.75.75 0 00-1.06-1.06l-5.97 5.97-2.47-2.47a.75.75 0 00-1.06 1.06l3 3a.75.75 0 001.06 0l6.5-6.5z"/><path fill-rule="evenodd" d="M3.75 2A1.75 1.75 0 002 3.75v16.5c0 .966.784 1.75 1.75 1.75h16.5A1.75 1.75 0 0022 20.25V3.75A1.75 1.75 0 0020.25 2H3.75zM3.5 3.75a.25.25 0 01.25-.25h16.5a.25.25 0 01.25.25v16.5a.25.25 0 01-.25.25H3.75a.25.25 0 01-.25-.25V3.75z"/></svg>
\ No newline at end of file
+<svg xmlns="http://www.w3.org/2000/svg" width="24" height="24" viewBox="0 0 24 24"><path fill-rule="evenodd" d="M3 6a1 1 0 011-1h5a1 1 0 011 1v5a1 1 0 01-1 1H4a1 1 0 01-1-1V6zm1.5 4.5v-4h4v4h-4z"/><path d="M12.75 5.5a.75.75 0 000 1.5h7.5a.75.75 0 000-1.5h-7.5zm0 6a.75.75 0 000 1.5h7.5a.75.75 0 000-1.5h-7.5zm0 6a.75.75 0 000 1.5h7.5a.75.75 0 000-1.5h-7.5zm-2.97-2.53a.75.75 0 010 1.06l-3.5 3.5a.75.75 0 01-1.06 0l-2-2a.75.75 0 111.06-1.06l1.47 1.47 2.97-2.97a.75.75 0 011.06 0z"/></svg>
\ No newline at end of file