diff --git a/lua/oil/init.lua b/lua/oil/init.lua
index 68894b8..9f70d05 100644
--- a/lua/oil/init.lua
+++ b/lua/oil/init.lua
@@ -556,7 +556,11 @@ M.setup = function(opts)
       loading.set_loading(bufnr, true)
       local function finish(new_url)
         if new_url ~= params.file then
-          util.rename_buffer(bufnr, new_url)
+          if util.rename_buffer(bufnr, new_url) then
+            -- If the buffer was replaced then don't initialize it. It's dead. The replacement will
+            -- have BufReadCmd called for it
+            return
+          end
         end
         vim.cmd.doautocmd({ args = { "BufReadPre", params.file }, mods = { emsg_silent = true } })
         view.initialize(bufnr)
diff --git a/lua/oil/util.lua b/lua/oil/util.lua
index 9192d91..ad03170 100644
--- a/lua/oil/util.lua
+++ b/lua/oil/util.lua
@@ -87,12 +87,13 @@ end
 
 ---@param src_bufnr integer|string Buffer number or name
 ---@param dest_buf_name string
+---@return boolean True if the buffer was replaced instead of renamed
 M.rename_buffer = function(src_bufnr, dest_buf_name)
   if type(src_bufnr) == "string" then
     src_bufnr = vim.fn.bufadd(src_bufnr)
     if not vim.api.nvim_buf_is_loaded(src_bufnr) then
       vim.api.nvim_buf_delete(src_bufnr, {})
-      return
+      return false
     end
   end
 
@@ -107,7 +108,7 @@ M.rename_buffer = function(src_bufnr, dest_buf_name)
     if ok then
       -- Renaming the buffer creates a new buffer with the old name. Find it and delete it.
       vim.api.nvim_buf_delete(vim.fn.bufadd(bufname), {})
-      return
+      return false
     end
   end
 
@@ -116,20 +117,25 @@ M.rename_buffer = function(src_bufnr, dest_buf_name)
   if vim.bo[src_bufnr].buflisted then
     vim.bo[dest_bufnr].buflisted = true
   end
-  -- Find any windows with the old buffer and replace them
-  for _, winid in ipairs(vim.api.nvim_list_wins()) do
-    if vim.api.nvim_win_is_valid(winid) then
-      if vim.api.nvim_win_get_buf(winid) == src_bufnr then
-        vim.api.nvim_win_set_buf(winid, dest_bufnr)
+  -- If we're renaming a buffer that we're about to enter, this may be called before the buffer is
+  -- actually in the window. We need to wait to enter the buffer and _then_ replace it.
+  vim.schedule(function()
+    -- Find any windows with the old buffer and replace them
+    for _, winid in ipairs(vim.api.nvim_list_wins()) do
+      if vim.api.nvim_win_is_valid(winid) then
+        if vim.api.nvim_win_get_buf(winid) == src_bufnr then
+          vim.api.nvim_win_set_buf(winid, dest_bufnr)
+        end
       end
     end
-  end
-  if vim.bo[src_bufnr].modified then
-    local src_lines = vim.api.nvim_buf_get_lines(src_bufnr, 0, -1, true)
-    vim.api.nvim_buf_set_lines(dest_bufnr, 0, -1, true, src_lines)
-  end
-  -- Try to delete, but don't if the buffer has changes
-  pcall(vim.api.nvim_buf_delete, src_bufnr, {})
+    if vim.bo[src_bufnr].modified then
+      local src_lines = vim.api.nvim_buf_get_lines(src_bufnr, 0, -1, true)
+      vim.api.nvim_buf_set_lines(dest_bufnr, 0, -1, true, src_lines)
+    end
+    -- Try to delete, but don't if the buffer has changes
+    pcall(vim.api.nvim_buf_delete, src_bufnr, {})
+  end)
+  return true
 end
 
 ---@param count integer
diff --git a/tests/regression_spec.lua b/tests/regression_spec.lua
new file mode 100644
index 0000000..46eade8
--- /dev/null
+++ b/tests/regression_spec.lua
@@ -0,0 +1,20 @@
+require("plenary.async").tests.add_to_env()
+local test_util = require("tests.test_util")
+
+a.describe("regression tests", function()
+  after_each(function()
+    test_util.reset_editor()
+  end)
+  -- see https://github.com/stevearc/oil.nvim/issues/25
+  a.it("can edit dirs that will be renamed to an existing buffer", function()
+    vim.cmd.edit({ args = { "README.md" } })
+    vim.cmd.vsplit()
+    vim.cmd.edit({ args = { "%:p:h" } })
+    assert.equals("oil", vim.bo.filetype)
+    vim.cmd.wincmd({ args = { "p" } })
+    assert.equals("markdown", vim.bo.filetype)
+    vim.cmd.edit({ args = { "%:p:h" } })
+    a.util.sleep(10)
+    assert.equals("oil", vim.bo.filetype)
+  end)
+end)