diff --git a/rc/filetype/ruby.kak b/rc/filetype/ruby.kak
index 8c6dea3f..88844ded 100644
--- a/rc/filetype/ruby.kak
+++ b/rc/filetype/ruby.kak
@@ -156,7 +156,6 @@ define-command -hidden ruby-indent-on-char %{
         try %{ execute-keys -draft <a-x> <a-k> ^ \h * (elsif)  $ <ret> <a-a> i <a-semicolon> <a-?> ^ \h * (if)                                                    <ret> <a-S> 1<a-&> }
         try %{ execute-keys -draft <a-x> <a-k> ^ \h * (when)   $ <ret> <a-a> i <a-semicolon> <a-?> ^ \h * (case)                                                  <ret> <a-S> 1<a-&> }
         try %{ execute-keys -draft <a-x> <a-k> ^ \h * (rescue) $ <ret> <a-a> i <a-semicolon> <a-?> ^ \h * (begin|def)                                             <ret> <a-S> 1<a-&> }
-        try %{ execute-keys -draft <a-x> <a-k> ^ \h * (end)    $ <ret> <a-a> i <a-semicolon> <a-?> ^ \h * (begin|case|class|def|for|if|module|unless|until|while) <ret> <a-S> 1<a-&> }
     }
 }
 
@@ -174,7 +173,7 @@ define-command -hidden ruby-indent-on-new-line %{
 define-command -hidden ruby-insert-on-new-line %[
     evaluate-commands -no-hooks -draft -itersel %[
         # copy _#_ comment prefix and following white spaces
-        try %{ execute-keys -draft k <a-x> s '^\h*\K#\h*' <ret> y j <a-x><semicolon> P }
+        try %{ execute-keys -draft k <a-x> s ^\h*\K#\h* <ret> y jgi P }
         # wisely add end structure
         evaluate-commands -save-regs x %[
             try %{ execute-keys -draft k <a-x> s ^ \h + <ret> \" x y } catch %{ reg x '' }
diff --git a/test/indent/ruby/deindent-on-if-else-end/cmd b/test/indent/ruby/deindent-on-if-else-end/cmd
new file mode 100644
index 00000000..af7a7628
--- /dev/null
+++ b/test/indent/ruby/deindent-on-if-else-end/cmd
@@ -0,0 +1 @@
+c<ret>elsif<ret>else
diff --git a/test/indent/ruby/deindent-on-if-else-end/in b/test/indent/ruby/deindent-on-if-else-end/in
new file mode 100644
index 00000000..d2ff880a
--- /dev/null
+++ b/test/indent/ruby/deindent-on-if-else-end/in
@@ -0,0 +1 @@
+if%( )
diff --git a/test/indent/ruby/deindent-on-if-else-end/out b/test/indent/ruby/deindent-on-if-else-end/out
new file mode 100644
index 00000000..0c6e08ae
--- /dev/null
+++ b/test/indent/ruby/deindent-on-if-else-end/out
@@ -0,0 +1,4 @@
+if
+elsif
+else
+end
diff --git a/test/indent/ruby/deindent-on-if-else-end/rc b/test/indent/ruby/deindent-on-if-else-end/rc
new file mode 100644
index 00000000..934f7e83
--- /dev/null
+++ b/test/indent/ruby/deindent-on-if-else-end/rc
@@ -0,0 +1,3 @@
+source "%val{runtime}/colors/default.kak"
+source "%val{runtime}/rc/filetype/ruby.kak"
+set buffer filetype ruby
diff --git a/test/indent/ruby/insert-comment-hash/cmd b/test/indent/ruby/insert-comment-hash/cmd
new file mode 100644
index 00000000..1b9319dc
--- /dev/null
+++ b/test/indent/ruby/insert-comment-hash/cmd
@@ -0,0 +1 @@
+c<ret><esc><a-o>jo# comment3<ret>comment4<esc><a-o>jo#    indented<ret>indented2<esc><a-o>jodef f<ret># comment<ret>comment2<esc>j<a-o>jodef f<ret># comment<esc>hhhi<ret>
diff --git a/test/indent/ruby/insert-comment-hash/in b/test/indent/ruby/insert-comment-hash/in
new file mode 100644
index 00000000..450a9496
--- /dev/null
+++ b/test/indent/ruby/insert-comment-hash/in
@@ -0,0 +1 @@
+# Comment%( ) comment2
diff --git a/test/indent/ruby/insert-comment-hash/out b/test/indent/ruby/insert-comment-hash/out
new file mode 100644
index 00000000..b5683071
--- /dev/null
+++ b/test/indent/ruby/insert-comment-hash/out
@@ -0,0 +1,18 @@
+# Comment
+# comment2
+
+# comment3
+# comment4
+
+#    indented
+#    indented2
+
+def f
+    # comment
+    # comment2
+end
+
+def f
+    # comm
+    # ent
+end
diff --git a/test/indent/ruby/insert-comment-hash/rc b/test/indent/ruby/insert-comment-hash/rc
new file mode 100644
index 00000000..934f7e83
--- /dev/null
+++ b/test/indent/ruby/insert-comment-hash/rc
@@ -0,0 +1,3 @@
+source "%val{runtime}/colors/default.kak"
+source "%val{runtime}/rc/filetype/ruby.kak"
+set buffer filetype ruby
diff --git a/test/regression/4086-ruby-deindenting-other-lines-than-keywords/cmd b/test/regression/4086-ruby-deindenting-other-lines-than-keywords/cmd
new file mode 100644
index 00000000..af092ecb
--- /dev/null
+++ b/test/regression/4086-ruby-deindenting-other-lines-than-keywords/cmd
@@ -0,0 +1 @@
+c<space><space>end
diff --git a/test/regression/4086-ruby-deindenting-other-lines-than-keywords/in b/test/regression/4086-ruby-deindenting-other-lines-than-keywords/in
new file mode 100644
index 00000000..115984bf
--- /dev/null
+++ b/test/regression/4086-ruby-deindenting-other-lines-than-keywords/in
@@ -0,0 +1,6 @@
+class MyClass
+  def method
+%( )
+
+  expression
+end
diff --git a/test/regression/4086-ruby-deindenting-other-lines-than-keywords/out b/test/regression/4086-ruby-deindenting-other-lines-than-keywords/out
new file mode 100644
index 00000000..52988874
--- /dev/null
+++ b/test/regression/4086-ruby-deindenting-other-lines-than-keywords/out
@@ -0,0 +1,6 @@
+class MyClass
+  def method
+  end
+
+  expression
+end
diff --git a/test/regression/4086-ruby-deindenting-other-lines-than-keywords/rc b/test/regression/4086-ruby-deindenting-other-lines-than-keywords/rc
new file mode 100644
index 00000000..934f7e83
--- /dev/null
+++ b/test/regression/4086-ruby-deindenting-other-lines-than-keywords/rc
@@ -0,0 +1,3 @@
+source "%val{runtime}/colors/default.kak"
+source "%val{runtime}/rc/filetype/ruby.kak"
+set buffer filetype ruby