diff --git a/middleman-cli/lib/middleman-cli/console.rb b/middleman-cli/lib/middleman-cli/console.rb
index 829e9901..4e267539 100644
--- a/middleman-cli/lib/middleman-cli/console.rb
+++ b/middleman-cli/lib/middleman-cli/console.rb
@@ -29,13 +29,13 @@ module Middleman::Cli
         ::Middleman::Logger.singleton(opts[:debug] ? 0 : 1, opts[:instrumenting] || false)
       end
 
-      interact_with @app
+      self.class.interact_with @app
     end
 
     # Start an interactive console in the context of the provided object.
     # @param [Object] context
     # @return [void]
-    def interact_with(context)
+    def self.interact_with(context)
       IRB.setup nil
       IRB.conf[:MAIN_CONTEXT] = IRB::Irb.new.context
       require 'irb/ext/multi-irb'
diff --git a/middleman-core/fixtures/asset-hash-app/source/subdir/index.html.erb b/middleman-core/fixtures/asset-hash-app/source/subdir/index.html.erb
index e9c2889c..79f12390 100644
--- a/middleman-core/fixtures/asset-hash-app/source/subdir/index.html.erb
+++ b/middleman-core/fixtures/asset-hash-app/source/subdir/index.html.erb
@@ -2,8 +2,17 @@
   <title>The Middleman!</title>
 <% end %>
 
+<h2>Abs</h2>
+<p>http://example.com/test.jpg</p>
+
 <h2>Image url:</h2>
-<p><%= image_path('100px.jpg') %></p>
+<p><img src="<%= image_path('100px.jpg') %>"></p>
+
+<h2>Image url2:</h2>
+<p><%= image_tag('200px.jpg') %></p>
+
+<h2>Image url3:</h2>
+<p><img src="/images/100px.jpg"></p>
 
 <h2>Autogenerated tests:</h2>
 <p>images/100px.jpg</p>
diff --git a/middleman-core/fixtures/asset-host-app/source/asset_host.html.erb b/middleman-core/fixtures/asset-host-app/source/asset_host.html.erb
index 3d7be098..41490760 100755
--- a/middleman-core/fixtures/asset-host-app/source/asset_host.html.erb
+++ b/middleman-core/fixtures/asset-host-app/source/asset_host.html.erb
@@ -19,4 +19,24 @@
 <%= image_tag "blank31.gif" %>
 <%= image_tag "blank32.gif" %>
 <%= image_tag "blank33.gif" %>
-<%= image_tag "blank34.gif" %>
\ No newline at end of file
+<%= image_tag "blank34.gif" %>
+<%= image_tag "blank100.gif" %>
+<%= image_tag "blank101.gif" %>
+<%= image_tag "blank102.gif" %>
+<%= image_tag "blank103.gif" %>
+<%= image_tag "blank104.gif" %>
+<%= image_tag "blank1010.gif" %>
+<%= image_tag "blank1021.gif" %>
+<%= image_tag "blank1032.gif" %>
+<%= image_tag "blank1043.gif" %>
+<%= image_tag "blank1054.gif" %>
+<%= image_tag "blank1020.gif" %>
+<%= image_tag "blank1021.gif" %>
+<%= image_tag "blank1022.gif" %>
+<%= image_tag "blank1023.gif" %>
+<%= image_tag "blank1024.gif" %>
+<%= image_tag "blank1030.gif" %>
+<%= image_tag "blank1031.gif" %>
+<%= image_tag "blank1032.gif" %>
+<%= image_tag "blank1033.gif" %>
+<%= image_tag "blank1034.gif" %>
\ No newline at end of file
diff --git a/middleman-core/lib/middleman-core/core_extensions/default_helpers.rb b/middleman-core/lib/middleman-core/core_extensions/default_helpers.rb
index e66c1739..71666bab 100644
--- a/middleman-core/lib/middleman-core/core_extensions/default_helpers.rb
+++ b/middleman-core/lib/middleman-core/core_extensions/default_helpers.rb
@@ -221,12 +221,12 @@ class Middleman::CoreExtensions::DefaultHelpers < ::Middleman::Extension
       url = url_for(url, options)
       super
     end
-    
+
     # Modified Padrino image_tag so that it finds the paths for srcset
     # using asset_path for the images listed in the srcset param
     def image_tag(path, params={})
       params.symbolize_keys!
-      
+
       if params.key?(:srcset)
         images_sources = params[:srcset].split(',').map do |src_def|
           if src_def.include?('//')
diff --git a/middleman-core/lib/middleman-core/extensions/asset_hash.rb b/middleman-core/lib/middleman-core/extensions/asset_hash.rb
index 39f1a069..07d58234 100644
--- a/middleman-core/lib/middleman-core/extensions/asset_hash.rb
+++ b/middleman-core/lib/middleman-core/extensions/asset_hash.rb
@@ -1,3 +1,4 @@
+require 'addressable/uri'
 require 'middleman-core/util'
 
 class Middleman::Extensions::AssetHash < ::Middleman::Extension
@@ -9,7 +10,6 @@ class Middleman::Extensions::AssetHash < ::Middleman::Extension
 
     require 'digest/sha1'
     require 'rack/mock'
-    require 'uri'
     require 'middleman-core/middleware/inline_url_rewriter'
   end
 
@@ -28,7 +28,8 @@ class Middleman::Extensions::AssetHash < ::Middleman::Extension
 
   Contract String, Or[String, Pathname], Any => Maybe[String]
   def rewrite_url(asset_path, dirpath, _request_path)
-    relative_path = Pathname.new(asset_path).relative?
+    uri = ::Addressable::URI.parse(asset_path)
+    relative_path = uri.path[0..0] != '/'
 
     full_asset_path = if relative_path
       dirpath.join(asset_path).to_s
@@ -36,10 +37,11 @@ class Middleman::Extensions::AssetHash < ::Middleman::Extension
       asset_path
     end
 
-    return unless asset_page = app.sitemap.find_resource_by_path(full_asset_path)
+    return unless asset_page = app.sitemap.find_resource_by_destination_path(full_asset_path) || app.sitemap.find_resource_by_path(full_asset_path)
 
     replacement_path = "/#{asset_page.destination_path}"
     replacement_path = Pathname.new(replacement_path).relative_path_from(dirpath).to_s if relative_path
+
     replacement_path
   end
 
@@ -56,7 +58,7 @@ class Middleman::Extensions::AssetHash < ::Middleman::Extension
     # This is so by the time we get around to the text files (which may reference
     # images and fonts) the static assets' hashes are already calculated.
     resources.sort_by do |a|
-      if %w(.svg).include? a.ext
+      if %w(.svg .svgz).include? a.ext
         0
       elsif %w(.js .css).include? a.ext
         1
@@ -73,9 +75,10 @@ class Middleman::Extensions::AssetHash < ::Middleman::Extension
     return if resource.ignored?
 
     # Render through the Rack interface so middleware and mounted apps get a shot
-    response = @rack_client.get(URI.escape(resource.destination_path),
-                                'bypass_inline_url_rewriter_asset_hash' => 'true'
-                               )
+    response = @rack_client.get(
+      URI.escape(resource.destination_path),
+      'bypass_inline_url_rewriter_asset_hash' => 'true'
+    )
 
     raise "#{resource.path} should be in the sitemap!" unless response.status == 200
 
@@ -87,6 +90,8 @@ class Middleman::Extensions::AssetHash < ::Middleman::Extension
 
   Contract IsA['Middleman::Sitemap::Resource'] => Bool
   def ignored_resource?(resource)
-    @ignore.any? { |ignore| Middleman::Util.path_match(ignore, resource.destination_path) }
+    @ignore.any? do |ignore|
+      Middleman::Util.path_match(ignore, resource.destination_path)
+    end
   end
 end
diff --git a/middleman-core/lib/middleman-core/extensions/asset_host.rb b/middleman-core/lib/middleman-core/extensions/asset_host.rb
index be161501..79e1813d 100644
--- a/middleman-core/lib/middleman-core/extensions/asset_host.rb
+++ b/middleman-core/lib/middleman-core/extensions/asset_host.rb
@@ -1,3 +1,4 @@
+require 'addressable/uri'
 require 'middleman-core/middleware/inline_url_rewriter'
 
 class Middleman::Extensions::AssetHost < ::Middleman::Extension
@@ -18,7 +19,8 @@ class Middleman::Extensions::AssetHost < ::Middleman::Extension
 
   Contract String, Or[String, Pathname], Any => String
   def rewrite_url(asset_path, dirpath, _request_path)
-    relative_path = Pathname.new(asset_path).relative?
+    uri = ::Addressable::URI.parse(asset_path)
+    relative_path = uri.path[0..0] != '/'
 
     full_asset_path = if relative_path
       dirpath.join(asset_path).to_s
diff --git a/middleman-core/lib/middleman-core/extensions/relative_assets.rb b/middleman-core/lib/middleman-core/extensions/relative_assets.rb
index 88c73af3..58ba20c3 100644
--- a/middleman-core/lib/middleman-core/extensions/relative_assets.rb
+++ b/middleman-core/lib/middleman-core/extensions/relative_assets.rb
@@ -1,3 +1,5 @@
+require 'addressable/uri'
+
 # Relative Assets extension
 class Middleman::Extensions::RelativeAssets < ::Middleman::Extension
   option :exts, %w(.css .png .jpg .jpeg .webp .svg .svgz .js .gif .ttf .otf .woff .woff2), 'List of extensions that get cache busters strings appended to them.'
@@ -22,7 +24,11 @@ class Middleman::Extensions::RelativeAssets < ::Middleman::Extension
 
   Contract String, Or[String, Pathname], Any => Maybe[String]
   def rewrite_url(asset_path, dirpath, request_path)
-    relative_path = Pathname.new(asset_path).relative?
+    uri = ::Addressable::URI.parse(asset_path)
+
+    return if uri.path[0..0] != '/'
+
+    relative_path = uri.host.nil?
 
     full_asset_path = if relative_path
       dirpath.join(asset_path).to_s
@@ -30,9 +36,9 @@ class Middleman::Extensions::RelativeAssets < ::Middleman::Extension
       asset_path
     end
 
-    return unless !full_asset_path.include?('//') && !asset_path.start_with?('data:')
-
     current_dir = Pathname(request_path).dirname
-    Pathname(full_asset_path).relative_path_from(current_dir).to_s
+    result = Pathname(full_asset_path).relative_path_from(current_dir).to_s
+
+    result
   end
 end
diff --git a/middleman-core/lib/middleman-core/middleware/inline_url_rewriter.rb b/middleman-core/lib/middleman-core/middleware/inline_url_rewriter.rb
index b1eddd11..34312060 100644
--- a/middleman-core/lib/middleman-core/middleware/inline_url_rewriter.rb
+++ b/middleman-core/lib/middleman-core/middleware/inline_url_rewriter.rb
@@ -1,7 +1,8 @@
-require 'middleman-core/util'
-require 'middleman-core/contracts'
 require 'rack'
 require 'rack/response'
+require 'addressable/uri'
+require 'middleman-core/util'
+require 'middleman-core/contracts'
 
 module Middleman
   module Middleware
@@ -51,10 +52,13 @@ module Middleman
 
         if path =~ /(^\/$)|(#{@source_exts_regex_text}$)/
           if body = ::Middleman::Util.extract_response_text(response)
+
             dirpath = Pathname.new(File.dirname(path))
 
             rewritten = ::Middleman::Util.rewrite_paths(body, path, @exts) do |asset_path|
-              relative_path = Pathname.new(asset_path).relative?
+              uri = ::Addressable::URI.parse(asset_path)
+
+              relative_path = uri.host.nil?
 
               full_asset_path = if relative_path
                 dirpath.join(asset_path).to_s
@@ -76,7 +80,7 @@ module Middleman
         [status, headers, response]
       end
 
-      Contract IGNORE_DESCRIPTOR => Bool
+      Contract IGNORE_DESCRIPTOR, String => Bool
       def should_ignore?(validator, value)
         if validator.is_a? Regexp
           # Treat as Regexp
diff --git a/middleman-core/lib/middleman-core/util.rb b/middleman-core/lib/middleman-core/util.rb
index debde48e..8a00eb9d 100644
--- a/middleman-core/lib/middleman-core/util.rb
+++ b/middleman-core/lib/middleman-core/util.rb
@@ -356,15 +356,10 @@ module Middleman
         opening_character = $1
         asset_path = $2
 
-        begin
-          uri = ::Addressable::URI.parse(asset_path)
-
-          if uri.relative? && result = yield(asset_path)
-            "#{opening_character}#{result}"
-          else
-            match
-          end
-        rescue
+        uri = ::Addressable::URI.parse(asset_path)
+        if uri.relative? && result = yield(asset_path)
+          "#{opening_character}#{result}"
+        else
           match
         end
       end