diff --git a/CHANGELOG.md b/CHANGELOG.md
index 01483d6b..938ef830 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,8 @@
   **this is a big one!** please report any issues :) #135
 * `if`/`unless`: invert if and unless with `!=` or `!==`, like we do for `!` and `not` #132
 * `@derive`: move `@derive` before `defstruct|schema|embedded_schema` declarations (fixes compiler warning!) #134
+* strings: rewrite double-quoted strings to use `~s` when there's 4+ escaped double-quotes
+  (`"\"\"\"\""` -> `~s("""")`) (`Credo.Check.Readability.StringSigils`) #146
 
 ### Fixes
 
diff --git a/README.md b/README.md
index 49ef2452..69dc6229 100644
--- a/README.md
+++ b/README.md
@@ -80,6 +80,7 @@ Disabling the rules means updating your `.credo.exs` depending on your configura
 {Credo.Check.Readability.SinglePipe, false},
 # **potentially breaks compilation** - see **Troubleshooting** section below
 {Credo.Check.Readability.StrictModuleLayout, false},
+{Credo.Check.Readability.StringSigils, false},
 {Credo.Check.Readability.UnnecessaryAliasExpansion, false},
 {Credo.Check.Readability.WithSingleClause, false},
 {Credo.Check.Refactor.CaseTrivialMatches, false},
diff --git a/lib/style/single_node.ex b/lib/style/single_node.ex
index a35bdee9..bc8fc692 100644
--- a/lib/style/single_node.ex
+++ b/lib/style/single_node.ex
@@ -18,6 +18,7 @@ defmodule Styler.Style.SingleNode do
   * Credo.Check.Readability.LargeNumbers
   * Credo.Check.Readability.ParenthesesOnZeroArityDefs
   * Credo.Check.Readability.PreferImplicitTry
+  * Credo.Check.Readability.StringSigils
   * Credo.Check.Readability.WithSingleClause
   * Credo.Check.Refactor.CaseTrivialMatches
   * Credo.Check.Refactor.CondStatements
@@ -27,6 +28,8 @@ defmodule Styler.Style.SingleNode do
 
   @behaviour Styler.Style
 
+  @closing_delimiters [~s|"|, ")", "}", "|", "]", "'", ">", "/"]
+
   alias Styler.Zipper
 
   def run({node, meta}, ctx), do: {:cont, {style(node), meta}, ctx}
@@ -34,10 +37,46 @@ defmodule Styler.Style.SingleNode do
   # as of 1.15, elixir's formatter takes care of this for us.
   if Version.match?(System.version(), "< 1.15.0-dev") do
     # 'charlist' => ~c"charlist"
-    defp style({:__block__, meta, [chars]} = node) when is_list(chars) do
-      if meta[:delimiter] == "'",
-        do: {:sigil_c, Keyword.put(meta, :delimiter, "\""), [{:<<>>, [line: meta[:line]], [List.to_string(chars)]}, []]},
-        else: node
+    defp style({:__block__, [{:delimiter, ~s|'|} | meta], [chars]}) when is_list(chars),
+      do: {:sigil_c, [{:delimiter, ~s|"|} | meta], [{:<<>>, [line: meta[:line]], [List.to_string(chars)]}, []]}
+  end
+
+  # rewrite double-quote strings with >= 4 escaped double-quotes as sigils
+  defp style({:__block__, [{:delimiter, ~s|"|} | meta], [string]} = node) when is_binary(string) do
+    # running a regex against every double-quote delimited string literal in a codebase doesn't have too much impact
+    # on adobe's internal codebase, but perhaps other codebases have way more literals where this'd have an impact?
+    if string =~ ~r/".*".*".*"/ do
+      # choose whichever delimiter would require the least # of escapes,
+      # ties being broken by our stylish ordering of delimiters (reflected in the 1-8 values)
+      {closer, _} =
+        string
+        |> String.codepoints()
+        |> Stream.filter(&(&1 in @closing_delimiters))
+        |> Stream.concat(@closing_delimiters)
+        |> Enum.frequencies()
+        |> Enum.min_by(fn
+          {~s|"|, count} -> {count, 1}
+          {")", count} -> {count, 2}
+          {"}", count} -> {count, 3}
+          {"|", count} -> {count, 4}
+          {"]", count} -> {count, 5}
+          {"'", count} -> {count, 6}
+          {">", count} -> {count, 7}
+          {"/", count} -> {count, 8}
+        end)
+
+      delimiter =
+        case closer do
+          ")" -> "("
+          "}" -> "{"
+          "]" -> "["
+          ">" -> "<"
+          closer -> closer
+        end
+
+      {:sigil_s, [{:delimiter, delimiter} | meta], [{:<<>>, [line: meta[:line]], [string]}, []]}
+    else
+      node
     end
   end
 
diff --git a/test/style/single_node_test.exs b/test/style/single_node_test.exs
index 97d4e0c6..cca3d92b 100644
--- a/test/style/single_node_test.exs
+++ b/test/style/single_node_test.exs
@@ -19,6 +19,22 @@ defmodule Styler.Style.SingleNodeTest do
     end
   end
 
+  test "string sigil rewrites" do
+    assert_style ~s|""|
+    assert_style ~s|"\\""|
+    assert_style ~s|"\\"\\""|
+    assert_style ~s|"\\"\\"\\""|
+    assert_style ~s|"\\"\\"\\"\\""|, ~s|~s("""")|
+    # choose closing delimiter wisely, based on what has the least conflicts, in the styliest order
+    assert_style ~s/"\\"\\"\\"\\" )"/, ~s/~s{"""" )}/
+    assert_style ~s/"\\"\\"\\"\\" })"/, ~s/~s|"""" })|/
+    assert_style ~s/"\\"\\"\\"\\" |})"/, ~s/~s["""" |})]/
+    assert_style ~s/"\\"\\"\\"\\" ]|})"/, ~s/~s'"""" ]|})'/
+    assert_style ~s/"\\"\\"\\"\\" ']|})"/, ~s/~s<"""" ']|})>/
+    assert_style ~s/"\\"\\"\\"\\" >']|})"/, ~s|~s/"""" >']\|})/|
+    assert_style ~s/"\\"\\"\\"\\" \/>']|})"/, ~s|~s("""" />']\|}\\))|
+  end
+
   test "{Map/Keyword}.merge with a single static key" do
     for module <- ~w(Map Keyword) do
       assert_style("#{module}.merge(foo, %{one_key: :bar})", "#{module}.put(foo, :one_key, :bar)")