diff --git a/lua/ivy/prompt.lua b/lua/ivy/prompt.lua
index f867d2e..b893ce1 100644
--- a/lua/ivy/prompt.lua
+++ b/lua/ivy/prompt.lua
@@ -1,60 +1,81 @@
 -- The prefix that will be before the search text for the user
 local prompt_prefix = ">> "
 
+-- Gets the suffix to delete from some text biased on what happens in a bash
+-- prompt. If the text dose not end in a letter then the last word and all of
+-- the tailing special characters will be returned. If the text dose end in a
+-- letter then only the last word will be returned leaving the special
+-- characters that are before the last word. For example
+--
+-- `some word` -> `some `
+-- `some     word` -> `some     `
+-- `some word       ` -> `some `
+local function get_delete_suffix(text)
+  if text:match "([A-Za-z]+)$" == nil then
+    return text:match "([A-Za-z]+[^A-Za-z]+)$"
+  end
+
+  return text:match "([A-Za-z]+)$"
+end
+
 local prompt = {}
 
 prompt.suffix = ""
 prompt.value = ""
 
 prompt.text = function()
   return prompt.value .. prompt.suffix
 end
+
 prompt.update = function()
   vim.api.nvim_echo({
     { prompt_prefix, "None" },
     { prompt.value:sub(1, -2), "None" },
     { prompt.value:sub(-1, -1), "Underlined" },
     { prompt.suffix, "None" },
   }, false, {})
 end
 
 prompt.input = function(char)
   if char == "BACKSPACE" then
     prompt.value = string.sub(prompt.value, 0, -2)
   elseif char == "LEFT" then
     if #prompt.value > 0 then
       prompt.suffix = prompt.value:sub(-1, -1) .. prompt.suffix
       prompt.value = prompt.value:sub(1, -2)
     end
   elseif char == "RIGHT" then
     if #prompt.suffix > 0 then
       prompt.value = prompt.value .. prompt.suffix:sub(1, 1)
       prompt.suffix = prompt.suffix:sub(2, -1)
     end
   elseif char == "DELETE_WORD" then
-    prompt.value = prompt.value:match "(.*)%s+.*$"
-    if prompt.value == nil then
+    local suffix = get_delete_suffix(prompt.value)
+
+    if suffix == nil then
       prompt.value = ""
+    else
+      prompt.value = prompt.value:sub(1, #prompt.value - #suffix)
     end
   elseif char == "\\\\" then
     prompt.value = prompt.value .. "\\"
   else
     prompt.value = prompt.value .. char
   end
 
   prompt.update()
 end
 
 prompt.set = function(value)
   prompt.value = value
   prompt.suffix = ""
   prompt.update()
 end
 
 prompt.destroy = function()
   prompt.value = ""
   prompt.suffix = ""
   vim.notify ""
 end
 
 return prompt
diff --git a/lua/ivy/prompt_test.lua b/lua/ivy/prompt_test.lua
index a99680d..ee834b6 100644
--- a/lua/ivy/prompt_test.lua
+++ b/lua/ivy/prompt_test.lua
@@ -1,61 +1,94 @@
 local prompt = require "ivy.prompt"
 local vim_mock = require "ivy.vim_mock"
 
 before_each(function()
   vim_mock.reset()
   prompt.destroy()
 end)
 
 -- Input a list of strings into the prompt
 local input = function(input_table)
   for index = 1, #input_table do
     prompt.input(input_table[index])
   end
 end
 
 -- Asserts the prompt contains the correct value
 local assert_prompt = function(t, expected)
   local text = prompt.text()
   if text ~= expected then
     t.error("The prompt text should be '" .. expected .. "' found '" .. text .. "'")
   end
 end
 
 it("starts with empty text", function(t)
   if prompt.text() ~= "" then
     t.error "The prompt should start with empty text"
   end
 end)
 
 it("can input some text", function(t)
   input { "A", "d", "e" }
   assert_prompt(t, "Ade")
 end)
 
 it("can delete a char", function(t)
   input { "A", "d", "e", "BACKSPACE" }
   assert_prompt(t, "Ad")
 end)
 
 it("will reset the text", function(t)
   input { "A", "d", "e" }
   prompt.set "New"
   assert_prompt(t, "New")
 end)
 
 it("can move around the a word", function(t)
   input { "P", "r", "o", "p", "t", "LEFT", "LEFT", "LEFT", "RIGHT", "m" }
   assert_prompt(t, "Prompt")
 end)
 
 it("can delete a word", function(t)
   prompt.set "Ade Attwood"
   input { "DELETE_WORD" }
-  assert_prompt(t, "Ade")
+  assert_prompt(t, "Ade ")
 end)
 
 it("can delete a word in the middle", function(t)
   prompt.set "Ade middle A"
   input { "LEFT", "LEFT", "DELETE_WORD" }
-  assert_prompt(t, "Ade A")
+  assert_prompt(t, "Ade  A")
+end)
+
+it("will delete the space and the word if the last word is single space", function(t)
+  prompt.set "some.thing "
+  input { "DELETE_WORD" }
+  assert_prompt(t, "some.")
 end)
+
+it("will only delete one word from path", function(t)
+  prompt.set "some/nested/path"
+  input { "DELETE_WORD" }
+  assert_prompt(t, "some/nested/")
+end)
+
+it("will delete tailing space", function(t)
+  prompt.set "word                 "
+  input { "DELETE_WORD" }
+  assert_prompt(t, "")
+end)
+
+it("will leave a random space", function(t)
+  prompt.set "some word       "
+  input { "DELETE_WORD" }
+  assert_prompt(t, "some ")
+end)
+
+local special_characters = { ".", "/", "^" }
+for _, char in ipairs(special_characters) do
+  it(string.format("will stop at a %s", char), function(t)
+    prompt.set(string.format("key%sValue", char))
+    input { "DELETE_WORD" }
+    assert_prompt(t, string.format("key%s", char))
+  end)
+end