diff --git a/runtime/lua/vim/_core/help.lua b/runtime/lua/vim/_core/help.lua
index cc410daf17..0dad8f93ff 100644
--- a/runtime/lua/vim/_core/help.lua
+++ b/runtime/lua/vim/_core/help.lua
@@ -39,7 +39,7 @@ local tag_exceptions = {
   ['expr-<=?'] = '<=?',
   ['expr-<?'] = '<?',
   ['expr-==?'] = '==?',
-  ['expr-=~?'] = '=~?',
+  ['expr-=~?'] = '=\\~?',
   ['expr->=?'] = '>=?',
   ['expr->?'] = '>?',
   ['expr-is?'] = 'is?',
@@ -103,12 +103,16 @@ function M.escape_subject(word)
 
     -- Change caret notation to 'CTRL-', except '^_'
     -- E.g. 'i^G^J' --> 'iCTRL-GCTRL-J'
-    word = word:gsub('%^([^_])', 'CTRL-%1')
+    -- Only treat '^' as control notation when followed by a caret-notation
+    -- char (a letter or one of "?@[\]^{"); otherwise leave it literal so
+    -- patterns like ':set^=' are not wrongly split. '{' is included so
+    -- '^{char}' matches the 'CTRL-{char}' placeholder tag.
+    word = word:gsub('%^([%a?@\\[\\%]{^])', 'CTRL-%1')
     -- Add underscores around 'CTRL-X' characters
     -- E.g. 'iCTRL-GCTRL-J' --> 'i_CTRL-G_CTRL-J'
     -- Only exception: 'CTRL-{character}'
-    word = word:gsub('([^_])CTRL%-', '%1_CTRL-')
-    word = word:gsub('(CTRL%-[^{])([^-_\\])', '%1_%2')
+    word = word:gsub('([^-_])CTRL%-', '%1_CTRL-')
+    word = word:gsub('(CTRL%-[^{])([^%u_\\-])', '%1_%2')
 
     -- Skip function arguments
     -- E.g. 'abs({expr})' --> 'abs'
diff --git a/test/functional/ex_cmds/help_spec.lua b/test/functional/ex_cmds/help_spec.lua
index 9263e23e3a..dcba0ac872 100644
--- a/test/functional/ex_cmds/help_spec.lua
+++ b/test/functional/ex_cmds/help_spec.lua
@@ -110,6 +110,7 @@ describe(':help', function()
     check_tag('help :[range]', '*:[range]*')
     check_tag('help [<space>', '[<Space>')
     check_tag('help ]_^D', ']_CTRL-D')
+    check_tag('help :set^=', '*:set^=*')
 
     check_tag([[help $HOME]], [[*$HOME*]])
 
@@ -132,6 +133,12 @@ describe(':help', function()
     check_tag([[help i^x^y]], '*i_CTRL-X_CTRL-Y*')
     check_tag([[help CTRL-\_CTRL-N]], [[*CTRL-\_CTRL-N*]])
     check_tag([[help i_CTRL-U-default]], [[*i_CTRL-U-default*]])
+    check_tag([[help expr-=~?]], [[*expr-=~?*]])
+    check_tag([[help map-CTRL-C]], '*map-CTRL-C*')
+    check_tag([=[help telnet-CTRL-]]=], '*telnet-CTRL-]*')
+    check_tag([[help c_CTRL-SHIFT-V]], '*c_CTRL-SHIFT-V*')
+    check_tag([[help i_CTRL-SHIFT-V]], '*i_CTRL-SHIFT-V*')
+    check_tag([[help c_CTRL-SHIFT-Q]], '*c_CTRL-SHIFT-Q*')
 
     check_tag([[exe "help i\<C-\>\<C-G>"]], [[*i_CTRL-\_CTRL-G*]])
     check_tag([[exe "help \<C-V>"]], '*CTRL-V*')