diff --git a/lib/licenses.nix b/lib/licenses.nix
index 39d8272f7573..30ca31ff71f2 100644
--- a/lib/licenses.nix
+++ b/lib/licenses.nix
@@ -412,6 +412,11 @@ in mkLicense lset) ({
     fullName = "Detection Rule License 1.0";
   };
 
+  dtoa = {
+    spdxId = "dtoa";
+    fullName = "dtoa License";
+  };
+
   eapl = {
     fullName = "EPSON AVASYS PUBLIC LICENSE";
     url = "https://avasys.jp/hp/menu000000700/hpg000000603.htm";
@@ -1066,6 +1071,11 @@ in mkLicense lset) ({
     url = "https://sources.debian.org/copyright/license/debianutils/4.9.1/";
   };
 
+  smlnj = {
+    spdxId = "SMLNJ";
+    fullName = "Standard ML of New Jersey License";
+  };
+
   sspl = {
     shortName = "SSPL";
     fullName = "Server Side Public License";
@@ -1215,6 +1225,11 @@ in mkLicense lset) ({
     url = "https://mcj.sourceforge.net/authors.html#xfig";
   };
 
+  xinetd = {
+    spdxId = "xinetd";
+    fullName = "xinetd License";
+  };
+
   zlib = {
     spdxId = "Zlib";
     fullName = "zlib License";
@@ -1229,6 +1244,11 @@ in mkLicense lset) ({
     spdxId = "ZPL-2.1";
     fullName = "Zope Public License 2.1";
   };
+
+  xskat = {
+    spdxId = "XSkat";
+    fullName = "XSkat License";
+  };
 } // {
   # TODO: remove legacy aliases
   agpl3 = {
diff --git a/pkgs/applications/audio/virtual-ans/default.nix b/pkgs/applications/audio/virtual-ans/default.nix
index 07f006aa0cc1..a14d5c5a37e2 100644
--- a/pkgs/applications/audio/virtual-ans/default.nix
+++ b/pkgs/applications/audio/virtual-ans/default.nix
@@ -81,7 +81,7 @@ stdenv.mkDerivation rec {
       '';
     homepage = "https://warmplace.ru/soft/ans/";
     sourceProvenance = with sourceTypes; [ binaryNativeCode ];
-    license = licenses.free;
+    license = licenses.unfreeRedistributable;
     # I cannot test the Darwin version, so I'll leave it disabled
     platforms = [ "x86_64-linux" "i686-linux" ];
     maintainers = with maintainers; [ jacg ];
diff --git a/pkgs/applications/misc/taskopen/default.nix b/pkgs/applications/misc/taskopen/default.nix
index 88050d2f449d..54361a0fbbd5 100644
--- a/pkgs/applications/misc/taskopen/default.nix
+++ b/pkgs/applications/misc/taskopen/default.nix
@@ -35,7 +35,7 @@ stdenv.mkDerivation rec {
     description = "Script for taking notes and open urls with taskwarrior";
     homepage = "https://github.com/ValiValpas/taskopen";
     platforms = platforms.linux;
-    license = licenses.free;
+    license = licenses.gpl2Plus;
     maintainers = [ maintainers.winpat ];
   };
 }
diff --git a/pkgs/applications/misc/vue/default.nix b/pkgs/applications/misc/vue/default.nix
index 41ab85bbd5c5..678aa886ce90 100644
--- a/pkgs/applications/misc/vue/default.nix
+++ b/pkgs/applications/misc/vue/default.nix
@@ -23,7 +23,7 @@ stdenv.mkDerivation rec {
     maintainers = with lib.maintainers; [ raskin ];
     platforms = with lib.platforms; linux;
     sourceProvenance = with lib.sourceTypes; [ binaryBytecode ];
-    license = lib.licenses.free; # Apache License fork, actually
+    license = lib.licenses.ecl20;
     mainProgram = "vue";
   };
 }
diff --git a/pkgs/applications/misc/xfontsel/default.nix b/pkgs/applications/misc/xfontsel/default.nix
index ecafb9d5118c..6bcab225c25a 100644
--- a/pkgs/applications/misc/xfontsel/default.nix
+++ b/pkgs/applications/misc/xfontsel/default.nix
@@ -32,7 +32,7 @@ stdenv.mkDerivation rec {
   meta = with lib; {
     homepage = "https://www.x.org/";
     description = "Allows testing the fonts available in an X server";
-    license = licenses.free;
+    license = with licenses; [ x11 smlnj mit ];
     maintainers = with maintainers; [ viric ];
     platforms = platforms.unix;
   };
diff --git a/pkgs/data/fonts/ubuntu-font-family/default.nix b/pkgs/data/fonts/ubuntu-font-family/default.nix
index 331e34690a5e..671ba8b4b48d 100644
--- a/pkgs/data/fonts/ubuntu-font-family/default.nix
+++ b/pkgs/data/fonts/ubuntu-font-family/default.nix
@@ -25,7 +25,7 @@ stdenvNoCC.mkDerivation rec {
     contemporary style and contains characteristics unique to
     the Ubuntu brand that convey a precise, reliable and free attitude.";
     homepage = "http://font.ubuntu.com/";
-    license = licenses.free;
+    license = licenses.ufl;
     platforms = platforms.all;
     maintainers = [ maintainers.antono ];
   };
diff --git a/pkgs/data/fonts/vdrsymbols/default.nix b/pkgs/data/fonts/vdrsymbols/default.nix
index 5df82b31cfe5..fd7aba9ec063 100644
--- a/pkgs/data/fonts/vdrsymbols/default.nix
+++ b/pkgs/data/fonts/vdrsymbols/default.nix
@@ -27,6 +27,6 @@ stdenvNoCC.mkDerivation rec {
     # Copyright (c) 2006 by Tavmjong Bah. All Rights Reserved.
     # DejaVu changes are in public domain
     # See https://dejavu-fonts.github.io/License.html for details
-    license = licenses.free;
+    license = with licenses; [ bitstreamVera publicDomain ];
   };
 }
diff --git a/pkgs/development/libraries/tinyxml/2.6.2.nix b/pkgs/development/libraries/tinyxml/2.6.2.nix
index 6589e718f10e..ded5013cca99 100644
--- a/pkgs/development/libraries/tinyxml/2.6.2.nix
+++ b/pkgs/development/libraries/tinyxml/2.6.2.nix
@@ -85,7 +85,7 @@ in stdenv.mkDerivation {
   meta = {
     description = "Simple, small, C++ XML parser that can be easily integrating into other programs";
     homepage = "http://www.grinninglizard.com/tinyxml/index.html";
-    license = lib.licenses.free;
+    license = lib.licenses.zlib;
     platforms = lib.platforms.unix;
   };
 }
diff --git a/pkgs/games/xskat/default.nix b/pkgs/games/xskat/default.nix
index 6baf397ad678..0d9fc5fe312f 100644
--- a/pkgs/games/xskat/default.nix
+++ b/pkgs/games/xskat/default.nix
@@ -23,7 +23,7 @@ stdenv.mkDerivation rec {
   meta = with lib; {
     description = "Famous german card game";
     platforms = platforms.unix;
-    license = licenses.free;
+    license = licenses.xskat;
     longDescription = "Play the german card game Skat against the AI or over IRC.";
     homepage = "https://web.archive.org/web/20221003060115/https://www.xskat.de/xskat.html";
   };
diff --git a/pkgs/servers/u9fs/default.nix b/pkgs/servers/u9fs/default.nix
index 9056b4791672..cb85a972e034 100644
--- a/pkgs/servers/u9fs/default.nix
+++ b/pkgs/servers/u9fs/default.nix
@@ -19,7 +19,7 @@ stdenv.mkDerivation {
   meta = with lib; {
     description = "Serve 9P from Unix";
     homepage = "http://p9f.org/magic/man2html?man=u9fs&sect=4";
-    license = licenses.free;
+    license = licenses.dtoa;
     maintainers = [ maintainers.ehmry ];
     platforms = platforms.unix;
     mainProgram = "u9fs";
diff --git a/pkgs/servers/xinetd/default.nix b/pkgs/servers/xinetd/default.nix
index 83cd3e45d9b2..9abef85bde29 100644
--- a/pkgs/servers/xinetd/default.nix
+++ b/pkgs/servers/xinetd/default.nix
@@ -26,7 +26,7 @@ stdenv.mkDerivation (finalAttrs: {
     description = "Secure replacement for inetd";
     platforms = lib.platforms.linux;
     homepage = "https://github.com/openSUSE/xinetd";
-    license = lib.licenses.free;
+    license = lib.licenses.xinetd;
     maintainers = with lib.maintainers; [ fgaz ];
   };
 })
diff --git a/pkgs/tools/graphics/welkin/default.nix b/pkgs/tools/graphics/welkin/default.nix
index 111abc745be5..e825f5e5d2b8 100644
--- a/pkgs/tools/graphics/welkin/default.nix
+++ b/pkgs/tools/graphics/welkin/default.nix
@@ -32,7 +32,7 @@ stdenv.mkDerivation rec {
     ];
     hydraPlatforms = [];
     sourceProvenance = with lib.sourceTypes; [ binaryBytecode ];
-    license = lib.licenses.free;
+    license = lib.licenses.bsd3;
     platforms = with lib.platforms; unix;
   };
 }
diff --git a/pkgs/tools/misc/tty-clock/default.nix b/pkgs/tools/misc/tty-clock/default.nix
index 32701caa64de..0abb0c668be0 100644
--- a/pkgs/tools/misc/tty-clock/default.nix
+++ b/pkgs/tools/misc/tty-clock/default.nix
@@ -30,7 +30,7 @@ stdenv.mkDerivation rec {
   meta = with lib; {
     broken = stdenv.isDarwin;
     homepage = "https://github.com/xorg62/tty-clock";
-    license = licenses.free;
+    license = licenses.bsd3;
     description = "Digital clock in ncurses";
     platforms = platforms.all;
     maintainers = [ maintainers.koral ];