diff --git a/src/nvim/register.c b/src/nvim/register.c
index 0012e4b44c..2f975b596b 100644
--- a/src/nvim/register.c
+++ b/src/nvim/register.c
@@ -539,19 +539,19 @@ static int put_in_typebuf(char *s, bool esc, bool colon, int silent)
 /// used only after other typeahead has been processed.
 static void put_reedit_in_typebuf(int silent)
 {
-  uint8_t buf[3];
-
   if (restart_edit == NUL) {
     return;
   }
 
-  if (restart_edit == 'V') {
-    buf[0] = 'g';
-    buf[1] = 'R';
-    buf[2] = NUL;
-  } else {
-    buf[0] = (uint8_t)(restart_edit == 'I' ? 'i' : restart_edit);
-    buf[1] = NUL;
+  uint8_t buf[] = { K_SPECIAL, KS_EXTRA, KE_COMMAND,
+                    // :startinsert
+                    's', 't', 'a', 'r', 't', 'i', CAR, NUL };
+  if (restart_edit == 'R') {
+    buf[8] = 'r';  // :startreplace
+  } else if (restart_edit == 'V') {
+    buf[8] = 'g';  // :startgreplace
+  } else if (restart_edit == 'A') {
+    buf[8] = '!';  // :startinsert!
   }
   if (ins_typebuf((char *)buf, REMAP_NONE, 0, true, silent) == OK) {
     restart_edit = NUL;
diff --git a/test/old/testdir/test_registers.vim b/test/old/testdir/test_registers.vim
index 51b332c220..720ce34ebc 100644
--- a/test/old/testdir/test_registers.vim
+++ b/test/old/testdir/test_registers.vim
@@ -529,21 +529,41 @@ func Test_clipboard_regs()
   bwipe!
 endfunc
 
-" Test for restarting the current mode (insert or virtual replace) after
+" Test for restarting the current mode (insert or (virtual) replace) after
 " executing the contents of a register
-func Test_put_reg_restart_mode()
+func Test_exec_reg_restart_mode()
   new
-  call append(0, 'editor')
-  normal gg
+
   let @r = "ivim \<Esc>"
-  call feedkeys("i\<C-O>@r\<C-R>=mode()\<CR>", 'xt')
+
+  call setline(1, 'editor')
+  normal gg
+  call feedkeys("i\<C-O>@r\<C-R>=mode(1)\<CR>", 'xt')
   call assert_equal('vimi editor', getline(1))
 
   call setline(1, 'editor')
   normal gg
-  call feedkeys("gR\<C-O>@r\<C-R>=mode()\<CR>", 'xt')
+  call feedkeys("R\<C-O>@r\<C-R>=mode(1)\<CR>", 'xt')
   call assert_equal('vimReditor', getline(1))
 
+  call setline(1, 'editor')
+  normal gg
+  call feedkeys("gR\<C-O>@r\<C-R>=mode(1)\<CR>", 'xt')
+  call assert_equal('vimRvditor', getline(1))
+
+  " If the register doesn't return to Normal mode, Vim should stay in whatever
+  " mode the register ends up with, and should not insert extra text. #20085
+  for [s0, expected] in
+        \ [['i', 'vim editor,i'], ['R', 'vim or,R'], ['gR', 'vim or,Rv']]
+    let @r = $"{s0}vim "
+    for s1 in ['i', 'R', 'gR']
+      call setline(1, 'editor')
+      normal gg
+      call feedkeys($"{s1}\<C-O>@r\<End>,\<C-R>=mode(1)\<CR>", 'xt')
+      call assert_equal(expected, getline(1))
+    endfor
+  endfor
+
   bwipe!
 endfunc