diff --git a/pkgs/tools/misc/lolcat/Gemfile.lock b/pkgs/tools/misc/lolcat/Gemfile.lock
index 58f62b64e71..e1e60663a27 100644
--- a/pkgs/tools/misc/lolcat/Gemfile.lock
+++ b/pkgs/tools/misc/lolcat/Gemfile.lock
@@ -1,13 +1,13 @@
 GEM
   remote: http://rubygems.org/
   specs:
-    lolcat (99.9.19)
+    lolcat (99.9.69)
       manpages (~> 0.6.1)
+      optimist (~> 3.0.0)
       paint (~> 2.0.0)
-      trollop (~> 2.1.3)
     manpages (0.6.1)
-    paint (2.0.1)
-    trollop (2.1.3)
+    optimist (3.0.0)
+    paint (2.0.3)
 
 PLATFORMS
   ruby
@@ -16,4 +16,4 @@ DEPENDENCIES
   lolcat
 
 BUNDLED WITH
-   1.14.6
+   1.16.3
diff --git a/pkgs/tools/misc/lolcat/gemset.nix b/pkgs/tools/misc/lolcat/gemset.nix
index 3e68f307530..9e351eecb82 100644
--- a/pkgs/tools/misc/lolcat/gemset.nix
+++ b/pkgs/tools/misc/lolcat/gemset.nix
@@ -1,12 +1,12 @@
 {
   lolcat = {
-    dependencies = ["manpages" "paint" "trollop"];
+    dependencies = ["manpages" "optimist" "paint"];
     source = {
       remotes = ["http://rubygems.org"];
-      sha256 = "05zm92ad0ws9fklpz1xk94hy95argwana01c6rr2xbx2q4mcil9m";
+      sha256 = "0d1yh2ikyhyh7am4qznd6fzv2pyvk82xrnsrsbbyxzcqfz9x6aa9";
       type = "gem";
     };
-    version = "99.9.19";
+    version = "99.9.69";
   };
   manpages = {
     source = {
@@ -16,20 +16,20 @@
     };
     version = "0.6.1";
   };
+  optimist = {
+    source = {
+      remotes = ["http://rubygems.org"];
+      sha256 = "05jxrp3nbn5iilc1k7ir90mfnwc5abc9h78s5rpm3qafwqxvcj4j";
+      type = "gem";
+    };
+    version = "3.0.0";
+  };
   paint = {
     source = {
       remotes = ["http://rubygems.org"];
-      sha256 = "1gnh9cihc84w4xbw51pg15crjvhblbq6nkzljrp7kmn3434nsg0d";
+      sha256 = "0ldb269l3pzkihmsws19cr9h3l6naw8c2fqpav8ck3nllnyiv7r2";
       type = "gem";
     };
-    version = "2.0.1";
-  };
-  trollop = {
-    source = {
-      remotes = ["http://rubygems.org"];
-      sha256 = "1rzx9rkacpq58dsvbbzs4cpybls1v1h36xskkfs5q2askpdr00wq";
-      type = "gem";
-    };
-    version = "2.1.3";
+    version = "2.0.3";
   };
 }
\ No newline at end of file