diff --git a/lib/sprockets/asset.rb b/lib/sprockets/asset.rb
index 52d0072dc..ae8f29318 100644
--- a/lib/sprockets/asset.rb
+++ b/lib/sprockets/asset.rb
@@ -67,6 +67,13 @@ def digest_path
       logical_path.sub(/\.(\w+)$/) { |ext| "-#{etag}#{ext}" }
     end
 
+    # Public: Return load path + logical path with digest spliced in.
+    #
+    # Returns String.
+    def full_digest_path
+      File.join(@load_path, digest_path)
+    end
+
     # Public: Returns String MIME type of asset. Returns nil if type is unknown.
     attr_reader :content_type
 
diff --git a/lib/sprockets/path_utils.rb b/lib/sprockets/path_utils.rb
index 467917de8..6e7555b43 100644
--- a/lib/sprockets/path_utils.rb
+++ b/lib/sprockets/path_utils.rb
@@ -6,6 +6,7 @@ module Sprockets
   # when code actually wants to reference ::FileUtils.
   module PathUtils
     extend self
+    require 'pathname'
 
     # Public: Like `File.stat`.
     #
@@ -73,8 +74,6 @@ def entries(path)
     #
     # Returns true if path is absolute, otherwise false.
     if File::ALT_SEPARATOR
-      require 'pathname'
-
       # On Windows, ALT_SEPARATOR is \
       # Delegate to Pathname since the logic gets complex.
       def absolute_path?(path)
@@ -102,6 +101,18 @@ def relative_path?(path)
       path =~ /^\.\.?($|#{SEPARATOR_PATTERN})/ ? true : false
     end
 
+    # Public: Get relative path from `start` to `dest`.
+    #
+    # start - String start path (file or dir)
+    # dest  - String destination path
+    #
+    # Returns relative String path from `start` to `dest`
+    def relative_path_from(start, dest)
+      start, dest = Pathname.new(start), Pathname.new(dest)
+      start = start.dirname unless start.directory?
+      dest.relative_path_from(start).to_s
+    end
+
     # Internal: Get relative path for root path and subpath.
     #
     # path    - String path
diff --git a/lib/sprockets/source_map_comment_processor.rb b/lib/sprockets/source_map_comment_processor.rb
index 6cc3337f7..c48622f16 100644
--- a/lib/sprockets/source_map_comment_processor.rb
+++ b/lib/sprockets/source_map_comment_processor.rb
@@ -21,8 +21,10 @@ def self.call(input)
       uri, _ = env.resolve!(input[:filename], accept: map_type)
       map = env.load(uri)
 
+      path = PathUtils.relative_path_from(input[:filename], map.full_digest_path)
+
       asset.metadata.merge(
-        data: asset.source + (comment % map.digest_path),
+        data: asset.source + (comment % path),
         links: asset.links + [asset.uri, map.uri]
       )
     end
diff --git a/lib/sprockets/source_map_utils.rb b/lib/sprockets/source_map_utils.rb
index 71a509f69..02b32d417 100644
--- a/lib/sprockets/source_map_utils.rb
+++ b/lib/sprockets/source_map_utils.rb
@@ -1,5 +1,6 @@
 # frozen_string_literal: true
 require 'json'
+require 'sprockets/path_utils'
 
 module Sprockets
   module SourceMapUtils
@@ -136,6 +137,9 @@ def encode_json_source_map(mappings, sources: nil, names: nil, filename: nil)
       case mappings
       when String
       when Array
+        mappings.each do |m|
+          m[:source] = PathUtils.relative_path_from(filename, m[:source])
+        end if filename
         sources ||= mappings.map { |m| m[:source] }.uniq.compact
         names   ||= mappings.map { |m| m[:name] }.uniq.compact
         mappings = encode_vlq_mappings(mappings, sources: sources, names: names)
diff --git a/test/test_source_maps.rb b/test/test_source_maps.rb
index 053eb1ade..698e93668 100644
--- a/test/test_source_maps.rb
+++ b/test/test_source_maps.rb
@@ -61,13 +61,13 @@ def setup
       map_2 = JSON.parse(@env['dynamic/application.js.map'].source)
 
       assert_equal([
-        "dynamic/unstable.source-43b85c2116b8c894a292c17a6845aa1c9b1491f7dc6bddf764c384668457d55a.js",
-        "dynamic/application.source-5cc94f82fada13ee8ef969d4cef2018e52ce42f9e1c8ccb6f8333cdc0dd5d3b5.coffee"
+        "unstable.source-43b85c2116b8c894a292c17a6845aa1c9b1491f7dc6bddf764c384668457d55a.js",
+        "application.source-5cc94f82fada13ee8ef969d4cef2018e52ce42f9e1c8ccb6f8333cdc0dd5d3b5.coffee"
       ], map_1["sources"])
 
       assert_equal([
-        "dynamic/unstable.source-2ae6f42425799bc9f718842df81be58c5f011dc93a00ca4da17be8877bdb02b3.js",
-        "dynamic/application.source-5cc94f82fada13ee8ef969d4cef2018e52ce42f9e1c8ccb6f8333cdc0dd5d3b5.coffee"
+        "unstable.source-2ae6f42425799bc9f718842df81be58c5f011dc93a00ca4da17be8877bdb02b3.js",
+        "application.source-5cc94f82fada13ee8ef969d4cef2018e52ce42f9e1c8ccb6f8333cdc0dd5d3b5.coffee"
       ], map_2["sources"])
     end
   end
@@ -93,7 +93,7 @@ def setup
       "version" => 3,
       "file" => "coffee/main.js",
       "mappings" => "AACA;AAAA,MAAA,sDAAA;IAAA;;EAAA,MAAA,GAAW;;EACX,QAAA,GAAW;;EAGX,IAAgB,QAAhB;IAAA,MAAA,GAAS,CAAC,GAAV;;;EAGA,MAAA,GAAS,SAAC,CAAD;WAAO,CAAA,GAAI;EAAX;;EAGT,IAAA,GAAO,CAAC,CAAD,EAAI,CAAJ,EAAO,CAAP,EAAU,CAAV,EAAa,CAAb;;EAGP,IAAA,GACE;IAAA,IAAA,EAAQ,IAAI,CAAC,IAAb;IACA,MAAA,EAAQ,MADR;IAEA,IAAA,EAAQ,SAAC,CAAD;aAAO,CAAA,GAAI,MAAA,CAAO,CAAP;IAAX,CAFR;;;EAKF,IAAA,GAAO,SAAA;AACL,QAAA;IADM,uBAAQ;WACd,KAAA,CAAM,MAAN,EAAc,OAAd;EADK;;EAIP,IAAsB,8CAAtB;IAAA,KAAA,CAAM,YAAN,EAAA;;;EAGA,KAAA;;AAAS;SAAA,sCAAA;;mBAAA,IAAI,CAAC,IAAL,CAAU,GAAV;AAAA;;;AA1BT",
-      "sources" => ["coffee/main.source-2ee93f5e7f3b843c3002478375432cf923860432879315335f4b987c205057db.coffee"],
+      "sources" => ["main.source-2ee93f5e7f3b843c3002478375432cf923860432879315335f4b987c205057db.coffee"],
       "names" => []
     }, map)
   end
@@ -138,7 +138,7 @@ def setup
       "version" => 3,
       "file" => "babel/main.js",
       "mappings" => ";;;;;;;;;;AACA,IAAI,IAAI,GAAG,KAAK,CAAC,GAAG,CAAC,UAAA,CAAC;SAAI,CAAC,GAAG,CAAC;CAAA,CAAC,CAAC;AACjC,IAAI,IAAI,GAAG,KAAK,CAAC,GAAG,CAAC,UAAC,CAAC,EAAE,CAAC;SAAK,CAAC,GAAG,CAAC;CAAA,CAAC,CAAC;;IAEhC,WAAW;YAAX,WAAW;;AACJ,WADP,WAAW,CACH,QAAQ,EAAE,SAAS,EAAE;0BAD7B,WAAW;;AAEb,+BAFE,WAAW,6CAEP,QAAQ,EAAE,SAAS,EAAE;GAE5B;;eAJG,WAAW;;WAKT,gBAAC,MAAM,EAAE;AACb,iCANE,WAAW,wCAME;KAChB;;;WACmB,yBAAG;AACrB,aAAO,IAAI,KAAK,CAAC,OAAO,EAAE,CAAC;KAC5B;;;SAVG,WAAW;GAAS,KAAK,CAAC,IAAI;;AAapC,IAAI,SAAS,uBACV,MAAM,CAAC,QAAQ,0BAAG;MACb,GAAG,EAAM,GAAG,EAEV,IAAI;;;;AAFN,WAAG,GAAG,CAAC,EAAE,GAAG,GAAG,CAAC;;;AAEd,YAAI,GAAG,GAAG;;AACd,WAAG,GAAG,GAAG,CAAC;AACV,WAAG,IAAI,IAAI,CAAC;;eACN,GAAG;;;;;;;;;;;CAEZ,EACF,CAAA",
-      "sources" => ["babel/main.source-1acb9cf16a3e1ce0fe0a38491472a14a6a97281ceace4b67ec16a904be5fa1b9.es6"],
+      "sources" => ["main.source-1acb9cf16a3e1ce0fe0a38491472a14a6a97281ceace4b67ec16a904be5fa1b9.es6"],
       "names"=>[]
     }, map)
   end
@@ -188,7 +188,7 @@ def setup
       "version" => 3,
       "file" => "sass/main.css",
       "mappings" => "AACE,MAAG;EACD,MAAM,EAAE,CAAC;EACT,OAAO,EAAE,CAAC;EACV,UAAU,EAAE,IAAI;AAGlB,MAAG;EAAE,OAAO,EAAE,YAAY;AAE1B,KAAE;EACA,OAAO,EAAE,KAAK;EACd,OAAO,EAAE,QAAQ;EACjB,eAAe,EAAE,IAAI",
-      "sources" => ["sass/main.source-86fe07ad89fecbab307d376bcadfa23d65ad108e3735b564510246b705f6ced1.scss"],
+      "sources" => ["main.source-86fe07ad89fecbab307d376bcadfa23d65ad108e3735b564510246b705f6ced1.scss"],
       "names" => []
     }, map)
   end
@@ -221,8 +221,8 @@ def setup
       "file" => "sass/with-import.css",
       "mappings" => "AAAA,IAAK;EAAE,KAAK,EAAE,GAAG;;ACEjB,GAAI;EAAE,KAAK,EAAE,IAAI",
       "sources" => [
-        "sass/_imported.source-9767e91e9d4b0334e59a1d389e9801bc6a2c5c4a5500a3c2c7915687965b2c16.scss",
-        "sass/with-import.source-5d53742ba113ac26396986bf14ab5c7e19ef193e494d5d868a9362e3e057cb26.scss"
+        "_imported.source-9767e91e9d4b0334e59a1d389e9801bc6a2c5c4a5500a3c2c7915687965b2c16.scss",
+        "with-import.source-5d53742ba113ac26396986bf14ab5c7e19ef193e494d5d868a9362e3e057cb26.scss"
       ],
       "names" => []
     }, map)
@@ -291,7 +291,7 @@ def setup
       "version"  => 3,
       "file"     => "sass/main.css",
       "mappings" => "AAAA,AACE,GADC,CACD,EAAE,CAAC;EACD,MAAM,EAAE,CAAE;EACV,OAAO,EAAE,CAAE;EACX,UAAU,EAAE,IAAK,GAClB;;AALH,AAOE,GAPC,CAOD,EAAE,CAAC;EAAE,OAAO,EAAE,YAAa,GAAI;;AAPjC,AASE,GATC,CASD,CAAC,CAAC;EACA,OAAO,EAAE,KAAM;EACf,OAAO,EAAE,QAAS;EAClB,eAAe,EAAE,IAAK,GACvB",
-      "sources"  => ["sass/main.source-86fe07ad89fecbab307d376bcadfa23d65ad108e3735b564510246b705f6ced1.scss"],
+      "sources"  => ["main.source-86fe07ad89fecbab307d376bcadfa23d65ad108e3735b564510246b705f6ced1.scss"],
       "names"    => []
     }, map)
   end