diff --git a/package.json b/package.json
index 3cfa20969..f6329ca21 100644
--- a/package.json
+++ b/package.json
@@ -42,6 +42,7 @@
     "autoprefixer": "^9.4.5",
     "bytes": "^3.0.0",
     "chalk": "^2.4.1",
+    "detective": "^5.2.0",
     "fs-extra": "^8.0.0",
     "lodash": "^4.17.11",
     "node-emoji": "^1.8.1",
diff --git a/src/index.js b/src/index.js
index 11f1aba46..b86050c2e 100644
--- a/src/index.js
+++ b/src/index.js
@@ -4,6 +4,7 @@ import fs from 'fs'
 import _ from 'lodash'
 import postcss from 'postcss'
 
+import getModuleDependencies from './lib/getModuleDependencies'
 import registerConfigAsDependency from './lib/registerConfigAsDependency'
 import processTailwindFeatures from './processTailwindFeatures'
 import formatCSS from './lib/formatCSS'
@@ -49,7 +50,9 @@ const getConfigFunction = config => () => {
   }
 
   if (!_.isObject(config)) {
-    delete require.cache[require.resolve(config)]
+    getModuleDependencies(config).forEach(mdl => {
+      delete require.cache[require.resolve(mdl.file)]
+    })
   }
 
   return resolveConfig([
diff --git a/src/lib/getModuleDependencies.js b/src/lib/getModuleDependencies.js
new file mode 100644
index 000000000..3cb6760ff
--- /dev/null
+++ b/src/lib/getModuleDependencies.js
@@ -0,0 +1,30 @@
+import fs from 'fs'
+import path from 'path'
+import resolve from 'resolve'
+import detective from 'detective'
+
+function createModule(file) {
+  const source = fs.readFileSync(file, 'utf-8')
+  const requires = detective(source)
+
+  return { file, requires }
+}
+
+export default function getModuleDependencies(entryFile) {
+  const rootModule = createModule(entryFile)
+  const modules = [rootModule]
+
+  // Iterate over the modules, even when new
+  // ones are being added
+  for (const mdl of modules) {
+    mdl.requires.forEach(dep => {
+      const basedir = path.dirname(mdl.file)
+      const depPath = resolve.sync(dep, { basedir })
+      const depModule = createModule(depPath)
+
+      modules.push(depModule)
+    })
+  }
+
+  return modules
+}
diff --git a/src/lib/registerConfigAsDependency.js b/src/lib/registerConfigAsDependency.js
index e4660e68d..13f3a5f35 100644
--- a/src/lib/registerConfigAsDependency.js
+++ b/src/lib/registerConfigAsDependency.js
@@ -1,4 +1,5 @@
 import fs from 'fs'
+import getModuleDependencies from './getModuleDependencies'
 
 export default function(configFile) {
   if (!fs.existsSync(configFile)) {
@@ -6,10 +7,12 @@ export default function(configFile) {
   }
 
   return function(css, opts) {
-    opts.messages.push({
-      type: 'dependency',
-      file: configFile,
-      parent: css.source.input.file,
+    getModuleDependencies(configFile).forEach(mdl => {
+      opts.messages.push({
+        type: 'dependency',
+        parent: css.source.input.file,
+        file: mdl.file,
+      })
     })
   }
 }
diff --git a/yarn.lock b/yarn.lock
index 71a6c01dc..ddbf87647 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -954,11 +954,25 @@ acorn-jsx@^5.0.2:
   resolved "https://registry.yarnpkg.com/acorn-jsx/-/acorn-jsx-5.0.2.tgz#84b68ea44b373c4f8686023a551f61a21b7c4a4f"
   integrity sha512-tiNTrP1MP0QrChmD2DdupCr6HWSFeKVw5d/dHTu4Y7rkAkRhU/Dt7dphAfIUyxtHpl/eBVip5uTNSpQJHylpAw==
 
+acorn-node@^1.6.1:
+  version "1.8.2"
+  resolved "https://registry.yarnpkg.com/acorn-node/-/acorn-node-1.8.2.tgz#114c95d64539e53dede23de8b9d96df7c7ae2af8"
+  integrity sha512-8mt+fslDufLYntIoPAaIMUe/lrbrehIiwmR3t2k9LljIzoigEPF27eLk2hy8zSGzmR/ogr7zbRKINMo1u0yh5A==
+  dependencies:
+    acorn "^7.0.0"
+    acorn-walk "^7.0.0"
+    xtend "^4.0.2"
+
 acorn-walk@^6.0.1:
   version "6.2.0"
   resolved "https://registry.yarnpkg.com/acorn-walk/-/acorn-walk-6.2.0.tgz#123cb8f3b84c2171f1f7fb252615b1c78a6b1a8c"
   integrity sha512-7evsyfH1cLOCdAzZAd43Cic04yKydNx0cF+7tiA19p1XnLLPU4dpCQOqpjqwokFe//vS0QqfqqjCS2JkiIs0cA==
 
+acorn-walk@^7.0.0:
+  version "7.0.0"
+  resolved "https://registry.yarnpkg.com/acorn-walk/-/acorn-walk-7.0.0.tgz#c8ba6f0f1aac4b0a9e32d1f0af12be769528f36b"
+  integrity sha512-7Bv1We7ZGuU79zZbb6rRqcpxo3OY+zrdtloZWoyD8fmGX+FeXRjE+iuGkZjSXLVovLzrsvMGMy0EkwA0E0umxg==
+
 acorn@^5.5.3:
   version "5.7.3"
   resolved "https://registry.yarnpkg.com/acorn/-/acorn-5.7.3.tgz#67aa231bf8812974b85235a96771eb6bd07ea279"
@@ -1620,6 +1634,11 @@ define-property@^2.0.2:
     is-descriptor "^1.0.2"
     isobject "^3.0.1"
 
+defined@^1.0.0:
+  version "1.0.0"
+  resolved "https://registry.yarnpkg.com/defined/-/defined-1.0.0.tgz#c98d9bcef75674188e110969151199e39b1fa693"
+  integrity sha1-yY2bzvdWdBiOEQlpFRGZ45sfppM=
+
 delayed-stream@~1.0.0:
   version "1.0.0"
   resolved "https://registry.yarnpkg.com/delayed-stream/-/delayed-stream-1.0.0.tgz#df3ae199acadfb7d440aaae0b29e2272b24ec619"
@@ -1640,6 +1659,15 @@ detect-newline@^2.1.0:
   resolved "https://registry.yarnpkg.com/detect-newline/-/detect-newline-2.1.0.tgz#f41f1c10be4b00e87b5f13da680759f2c5bfd3e2"
   integrity sha1-9B8cEL5LAOh7XxPaaAdZ8sW/0+I=
 
+detective@^5.2.0:
+  version "5.2.0"
+  resolved "https://registry.yarnpkg.com/detective/-/detective-5.2.0.tgz#feb2a77e85b904ecdea459ad897cc90a99bd2a7b"
+  integrity sha512-6SsIx+nUUbuK0EthKjv0zrdnajCCXVYGmbYYiYjFVpzcjwEs/JMDZ8tPRG29J/HhN56t3GJp2cGSWDRjjot8Pg==
+  dependencies:
+    acorn-node "^1.6.1"
+    defined "^1.0.0"
+    minimist "^1.1.1"
+
 diff-sequences@^24.9.0:
   version "24.9.0"
   resolved "https://registry.yarnpkg.com/diff-sequences/-/diff-sequences-24.9.0.tgz#5715d6244e2aa65f48bba0bc972db0b0b11e95b5"
@@ -4968,6 +4996,11 @@ xml-name-validator@^3.0.0:
   resolved "https://registry.yarnpkg.com/xml-name-validator/-/xml-name-validator-3.0.0.tgz#6ae73e06de4d8c6e47f9fb181f78d648ad457c6a"
   integrity sha512-A5CUptxDsvxKJEU3yO6DuWBSJz/qizqzJKOMIfUJHETbBw/sFaDxgd6fxm1ewUaM0jZ444Fc5vC5ROYurg/4Pw==
 
+xtend@^4.0.2:
+  version "4.0.2"
+  resolved "https://registry.yarnpkg.com/xtend/-/xtend-4.0.2.tgz#bb72779f5fa465186b1f438f674fa347fdb5db54"
+  integrity sha512-LKYU1iAXJXUgAXn9URjiu+MWhyUXHsvfp7mcuYm9dSUKK0/CjtrUwFAxD82/mCWbtLsGjFIad0wIsod4zrTAEQ==
+
 y18n@^4.0.0:
   version "4.0.0"
   resolved "https://registry.yarnpkg.com/y18n/-/y18n-4.0.0.tgz#95ef94f85ecc81d007c264e190a120f0a3c8566b"