diff --git a/runtime/doc/lua.txt b/runtime/doc/lua.txt
index d1bd81eb92..f9767cbd68 100644
--- a/runtime/doc/lua.txt
+++ b/runtime/doc/lua.txt
@@ -3902,6 +3902,7 @@ versions (1.2.3-rc1) are not matched. >
     >1.2.3            greater than 1.2.3
     <1.2.3            before 1.2.3
     >=1.2.3           at least 1.2.3
+    <=1.2.3           at most 1.2.3
     ~1.2.3            is >=1.2.3 <1.3.0       "reasonably close to 1.2.3"
     ^1.2.3            is >=1.2.3 <2.0.0       "compatible with 1.2.3"
     ^0.2.3            is >=0.2.3 <0.3.0       (0.x.x is special)
@@ -3916,7 +3917,7 @@ versions (1.2.3-rc1) are not matched. >
     *                 any version
     x                 same
 
-    1.2.3 - 2.3.4     is >=1.2.3 <=2.3.4
+    1.2.3 - 2.3.4     is >=1.2.3 <2.3.4
 
     Partial right: missing pieces treated as x (2.3 => 2.3.x).
     1.2.3 - 2.3       is >=1.2.3 <2.4.0
diff --git a/runtime/lua/vim/version.lua b/runtime/lua/vim/version.lua
index 1aa7d4144d..dee99a22cc 100644
--- a/runtime/lua/vim/version.lua
+++ b/runtime/lua/vim/version.lua
@@ -28,6 +28,7 @@
 --- >1.2.3            greater than 1.2.3
 --- <1.2.3            before 1.2.3
 --- >=1.2.3           at least 1.2.3
+--- <=1.2.3           at most 1.2.3
 --- ~1.2.3            is >=1.2.3 <1.3.0       "reasonably close to 1.2.3"
 --- ^1.2.3            is >=1.2.3 <2.0.0       "compatible with 1.2.3"
 --- ^0.2.3            is >=0.2.3 <0.3.0       (0.x.x is special)
@@ -42,7 +43,7 @@
 --- *                 any version
 --- x                 same
 ---
---- 1.2.3 - 2.3.4     is >=1.2.3 <=2.3.4
+--- 1.2.3 - 2.3.4     is >=1.2.3 <2.3.4
 ---
 --- Partial right: missing pieces treated as x (2.3 => 2.3.x).
 --- 1.2.3 - 2.3       is >=1.2.3 <2.4.0
@@ -315,9 +316,23 @@ function M.range(spec) -- Adapted from https://github.com/folke/lazy.nvim
       from = M._version({})
     elseif mods == '<=' then
       from = M._version({})
-      to.patch = to.patch + 1
+      -- HACK: construct the smallest reasonable version bigger than `to`
+      -- to simulate `<=` while using exclusive right hand side
+      if to.prerelease then
+        to.prerelease = to.prerelease .. '.0'
+      else
+        to.patch = to.patch + 1
+        to.prerelease = '0'
+      end
     elseif mods == '>' then
-      from.patch = from.patch + 1
+      -- HACK: construct the smallest reasonable version bigger than `from`
+      -- to simulate `>` while using inclusive left hand side
+      if from.prerelease then
+        from.prerelease = from.prerelease .. '.0'
+      else
+        from.patch = from.patch + 1
+        from.prerelease = '0'
+      end
       to = nil
     elseif mods == '>=' then
       to = nil
diff --git a/test/functional/lua/version_spec.lua b/test/functional/lua/version_spec.lua
index e681690e52..31bdbcc914 100644
--- a/test/functional/lua/version_spec.lua
+++ b/test/functional/lua/version_spec.lua
@@ -58,10 +58,10 @@ describe('version', function()
       ['1.2.3'] = { from = { 1, 2, 3 }, to = { 1, 2, 3 } },
       ['1.2'] = { from = { 1, 2, 0 }, to = { 1, 3, 0 } },
       ['=1.2.3'] = { from = { 1, 2, 3 }, to = { 1, 2, 3 } },
-      ['>1.2.3'] = { from = { 1, 2, 4 } },
+      ['>1.2.3'] = { from = '1.2.4-0' },
       ['>=1.2.3'] = { from = { 1, 2, 3 } },
       ['<1.2.3'] = { from = { 0, 0, 0 }, to = { 1, 2, 3 } },
-      ['<=1.2.3'] = { from = { 0, 0, 0 }, to = { 1, 2, 4 } },
+      ['<=1.2.3'] = { from = { 0, 0, 0 }, to = '1.2.4-0' },
       ['~1.2.3'] = { from = { 1, 2, 3 }, to = { 1, 3, 0 } },
       ['^1.2.3'] = { from = { 1, 2, 3 }, to = { 2, 0, 0 } },
       ['^0.2.3'] = { from = { 0, 2, 3 }, to = { 0, 3, 0 } },
@@ -125,6 +125,17 @@ describe('version', function()
       assert(vim.version.range('>0.10'):has('0.12.0-dev'))
       assert(not vim.version.range('>=0.12'):has('0.12.0-dev'))
 
+      assert(not vim.version.range('<=1.2.3'):has('1.2.4-alpha'))
+      assert(not vim.version.range('<=1.2.3-0'):has('1.2.3'))
+      assert(not vim.version.range('<=1.2.3-alpha'):has('1.2.3'))
+      assert(not vim.version.range('<=1.2.3-1'):has('1.2.4-0'))
+      assert(vim.version.range('<=1.2.3-0'):has('1.2.3-0'))
+      assert(vim.version.range('<=1.2.3-alpha'):has('1.2.3-alpha'))
+
+      assert(vim.version.range('>1.2.3'):has('1.2.4-0'))
+      assert(vim.version.range('>1.2.3'):has('1.2.4-alpha'))
+      assert(vim.version.range('>1.2.3-0'):has('1.2.3-1'))
+
       local range_alpha = vim.version.range('1.2.3-alpha')
       eq(vim.version.range(tostring(range_alpha)), range_alpha)
     end)