diff --git a/src/helpers/headers.js b/src/helpers/headers.js
index c37701adf..7a37e8526 100644
--- a/src/helpers/headers.js
+++ b/src/helpers/headers.js
@@ -35,5 +35,23 @@ module.exports = {
    */
   hasHeader: (headers, name) => {
     return Boolean(Object.keys(headers).find(k => k.toLowerCase() === name.toLowerCase()))
+  },
+
+  /**
+   * Determines if a given mimetype is JSON, or a variant of such.
+   *
+   * @param {string}} mimeType
+   * @returns {boolean}
+   */
+  isMimeTypeJson: (mimeType) => {
+    return [
+      'application/json',
+      'application/x-json',
+      'text/json',
+      'text/x-json',
+      '+json'
+    ].some(function (type) {
+      return mimeType.indexOf(type) > -1
+    })
   }
 }
diff --git a/src/targets/shell/curl.js b/src/targets/shell/curl.js
index 3cde6bb5a..2b14b2fbc 100644
--- a/src/targets/shell/curl.js
+++ b/src/targets/shell/curl.js
@@ -11,7 +11,7 @@
 'use strict'
 
 const util = require('util')
-const helpers = require('../../helpers/shell')
+const helpers = require('./helpers')
 const headerHelpers = require('../../helpers/headers')
 const CodeBuilder = require('../../helpers/code-builder')
 
@@ -100,10 +100,38 @@ module.exports = function (source, options) {
     default:
       // raw request body
       if (source.postData.text) {
-        code.push(
-          '%s %s', opts.binary ? '--data-binary' : (opts.short ? '-d' : '--data'),
-          helpers.quote(source.postData.text)
-        )
+        let builtPayload = false
+
+        // If we're dealing with a JSON variant, and our payload is JSON let's make it look a little nicer.
+        if (headerHelpers.isMimeTypeJson(source.postData.mimeType)) {
+          // If our postData is less than 20 characters, let's keep it all on one line so as to not make the snippet
+          // overly lengthy.
+          if (source.postData.text.length > 20) {
+            try {
+              const jsonPayload = JSON.parse(source.postData.text)
+
+              // If the JSON object has a single quote we should prepare it inside of a HEREDOC because the single
+              // quote in something like `string's` can't be escaped when used with `--data`.
+              //
+              // Basically this boils down to `--data @- <<EOF...EOF` vs `--data '...'`.
+              builtPayload = true
+              code.push(
+                source.postData.text.indexOf("'") > 0 ? '%s @- <<EOF\n%s\nEOF' : "%s '\n%s\n'",
+                opts.binary ? '--data-binary' : (opts.short ? '-d' : '--data'),
+                JSON.stringify(jsonPayload, null, opts.indent)
+              )
+            } catch (err) {
+              // no-op
+            }
+          }
+        }
+
+        if (!builtPayload) {
+          code.push(
+            '%s %s', opts.binary ? '--data-binary' : (opts.short ? '-d' : '--data'),
+            helpers.quote(source.postData.text)
+          )
+        }
       }
   }
 
diff --git a/src/helpers/shell.js b/src/targets/shell/helpers.js
similarity index 100%
rename from src/helpers/shell.js
rename to src/targets/shell/helpers.js
diff --git a/src/targets/shell/httpie.js b/src/targets/shell/httpie.js
index 40b0338a3..61ac07293 100644
--- a/src/targets/shell/httpie.js
+++ b/src/targets/shell/httpie.js
@@ -11,7 +11,7 @@
 'use strict'
 
 const util = require('util')
-const shell = require('../../helpers/shell')
+const shell = require('./helpers')
 const CodeBuilder = require('../../helpers/code-builder')
 
 module.exports = function (source, options) {
diff --git a/src/targets/shell/wget.js b/src/targets/shell/wget.js
index a453cc855..cfc9f77e6 100644
--- a/src/targets/shell/wget.js
+++ b/src/targets/shell/wget.js
@@ -11,7 +11,7 @@
 'use strict'
 
 const util = require('util')
-const helpers = require('../../helpers/shell')
+const helpers = require('./helpers')
 const CodeBuilder = require('../../helpers/code-builder')
 
 module.exports = function (source, options) {
diff --git a/test/fixtures/curl/jsonObj-short.json b/test/fixtures/curl/jsonObj-short.json
new file mode 100644
index 000000000..730c0befc
--- /dev/null
+++ b/test/fixtures/curl/jsonObj-short.json
@@ -0,0 +1,14 @@
+{
+  "url": "http://mockbin.com/har",
+  "method": "POST",
+  "headers": [
+    {
+      "name": "content-type",
+      "value": "application/json"
+    }
+  ],
+  "postData": {
+    "text": "{\"foo\": \"bar\"}",
+    "mimeType": "application/json"
+  }
+}
diff --git a/test/fixtures/curl/jsonObj-with-singlequotes.json b/test/fixtures/curl/jsonObj-with-singlequotes.json
new file mode 100644
index 000000000..b08b79d6e
--- /dev/null
+++ b/test/fixtures/curl/jsonObj-with-singlequotes.json
@@ -0,0 +1,14 @@
+{
+  "method": "POST",
+  "url": "http://mockbin.com/har",
+  "headers": [
+    {
+      "name": "content-type",
+      "value": "application/json"
+    }
+  ],
+  "postData": {
+    "mimeType": "application/json",
+    "text": "{\"number\":1,\"string\":\"f'oo\"}"
+  }
+}
diff --git a/test/fixtures/output/shell/curl/application-json.sh b/test/fixtures/output/shell/curl/application-json.sh
index f7b19eb9f..39cec7912 100644
--- a/test/fixtures/output/shell/curl/application-json.sh
+++ b/test/fixtures/output/shell/curl/application-json.sh
@@ -1,4 +1,25 @@
 curl --request POST \
   --url http://mockbin.com/har \
   --header 'content-type: application/json' \
-  --data '{"number":1,"string":"f\"oo","arr":[1,2,3],"nested":{"a":"b"},"arr_mix":[1,"a",{"arr_mix_nested":{}}],"boolean":false}'
+  --data '
+{
+  "number": 1,
+  "string": "f\"oo",
+  "arr": [
+    1,
+    2,
+    3
+  ],
+  "nested": {
+    "a": "b"
+  },
+  "arr_mix": [
+    1,
+    "a",
+    {
+      "arr_mix_nested": {}
+    }
+  ],
+  "boolean": false
+}
+'
diff --git a/test/targets/shell/curl.js b/test/targets/shell/curl.js
index 9435639b0..b6738665a 100644
--- a/test/targets/shell/curl.js
+++ b/test/targets/shell/curl.js
@@ -72,4 +72,18 @@ module.exports = function (HTTPSnippet, fixtures) {
     result.should.be.a.String()
     result.replace(/\\\n/g, '').should.eql("curl --request POST @--url 'http://mockbin.com/har?foo=bar&foo=baz&baz=abc&key=value' @--header 'accept: application/json' @--header 'content-type: application/x-www-form-urlencoded' @--cookie 'foo=bar; bar=baz' @--data foo=bar")
   })
+
+  it('should send JSON-encoded data with single quotes within a HEREDOC', function () {
+    var result = new HTTPSnippet(fixtures.curl['jsonObj-with-singlequotes']).convert('shell', 'curl')
+
+    result.should.be.a.String()
+    result.replace(/\\\n/g, '').replace(/\n/g, '').should.eql("curl --request POST   --url http://mockbin.com/har   --header 'content-type: application/json'   --data @- <<EOF{  \"number\": 1,  \"string\": \"f'oo\"}EOF")
+  })
+
+  it('should keep JSON payloads that are smaller than 20 characters on one line', function () {
+    var result = new HTTPSnippet(fixtures.curl['jsonObj-short']).convert('shell', 'curl')
+
+    result.should.be.a.String()
+    result.replace(/\\\n/g, '').replace(/\n/g, '').should.eql("curl --request POST   --url http://mockbin.com/har   --header 'content-type: application/json'   --data '{\"foo\": \"bar\"}'")
+  })
 }