diff --git a/lib/Repository.js b/lib/Repository.js
index 74452dde..7823b099 100644
--- a/lib/Repository.js
+++ b/lib/Repository.js
@@ -231,13 +231,13 @@ class Repository extends Requestable {
     * Get tha sha for a particular object in the repository. This is a convenience function
     * @see https://developer.github.com/v3/repos/contents/#get-contents
     * @param {string} [branch] - the branch to look in, or the repository's default branch if omitted
-    * @param {string} path - the path of the file or directory
+    * @param {string} path - the unencoded path of the file or directory
     * @param {Requestable.callback} cb - will receive a description of the requested object, including a `SHA` property
     * @return {Promise} - the promise for the http request
     */
    getSha(branch, path, cb) {
       branch = branch ? `?ref=${branch}` : '';
-      return this._request('GET', `/repos/${this.__fullname}/contents/${path}${branch}`, null, cb);
+      return this._request('GET', `/repos/${this.__fullname}/contents/${encodeContentPath(path)}${branch}`, null, cb);
    }
 
    /**
@@ -499,13 +499,13 @@ class Repository extends Requestable {
     * Get the contents of a repository
     * @see https://developer.github.com/v3/repos/contents/#get-contents
     * @param {string} ref - the ref to check
-    * @param {string} path - the path containing the content to fetch
+    * @param {string} path - the unencoded path containing the content to fetch
     * @param {boolean} raw - `true` if the results should be returned raw instead of GitHub's normalized format
     * @param {Requestable.callback} cb - will receive the fetched data
     * @return {Promise} - the promise for the http request
     */
    getContents(ref, path, raw, cb) {
-      path = path ? `${encodeURI(path)}` : '';
+      path = encodeContentPath(path);
       return this._request('GET', `/repos/${this.__fullname}/contents/${path}`, {
          ref,
       }, cb, raw);
@@ -706,11 +706,12 @@ class Repository extends Requestable {
     * Delete a file from a branch
     * @see https://developer.github.com/v3/repos/contents/#delete-a-file
     * @param {string} branch - the branch to delete from, or the default branch if not specified
-    * @param {string} path - the path of the file to remove
+    * @param {string} path - the unencoded path of the file to remove
     * @param {Requestable.callback} cb - will receive the commit in which the delete occurred
     * @return {Promise} - the promise for the http request
     */
    deleteFile(branch, path, cb) {
+      const filePath = encodeContentPath(path);
       return this.getSha(branch, path)
          .then((response) => {
             const deleteCommit = {
@@ -718,7 +719,7 @@ class Repository extends Requestable {
                sha: response.data.sha,
                branch,
             };
-            return this._request('DELETE', `/repos/${this.__fullname}/contents/${path}`, deleteCommit, cb);
+            return this._request('DELETE', `/repos/${this.__fullname}/contents/${filePath}`, deleteCommit, cb);
          });
    }
 
@@ -755,7 +756,7 @@ class Repository extends Requestable {
     * Write a file to the repository
     * @see https://developer.github.com/v3/repos/contents/#update-a-file
     * @param {string} branch - the name of the branch
-    * @param {string} path - the path for the file
+    * @param {string} path - the unencoded path for the file
     * @param {string} content - the contents of the file
     * @param {string} message - the commit message
     * @param {Object} [options] - commit options
@@ -771,7 +772,7 @@ class Repository extends Requestable {
          cb = options;
          options = {};
       }
-      let filePath = path ? encodeURI(path) : '';
+      let filePath = encodeContentPath(path);
       let shouldEncode = options.encode !== false;
       let commit = {
          branch,
@@ -781,7 +782,7 @@ class Repository extends Requestable {
          content: shouldEncode ? Base64.encode(content) : content,
       };
 
-      return this.getSha(branch, filePath)
+      return this.getSha(branch, path)
          .then((response) => {
             commit.sha = response.data.sha;
             return this._request('PUT', `/repos/${this.__fullname}/contents/${filePath}`, commit, cb);
@@ -914,3 +915,12 @@ class Repository extends Requestable {
 }
 
 module.exports = Repository;
+
+/**
+ * Encode each component of a Contents API path while preserving directory separators.
+ * @param {string} path - an unencoded repository path
+ * @return {string} the path suitable for a Contents API URL
+ */
+function encodeContentPath(path) {
+   return path ? path.split('/').map(encodeURIComponent).join('/') : '';
+}
diff --git a/test/error.spec.js b/test/error.spec.js
index 9cfe5438..80bb0662 100644
--- a/test/error.spec.js
+++ b/test/error.spec.js
@@ -81,3 +81,61 @@ describe('Rate limit OK', function() {
       nock.cleanAll();
    });
 });
+
+describe('content path encoding', function() {
+   let github;
+   let repository;
+
+   beforeEach(function() {
+      github = new Github();
+      repository = github.getRepo('octo', 'release-notes');
+   });
+
+   afterEach(function() {
+      nock.cleanAll();
+   });
+
+   it('should encode reserved characters when getting contents', function() {
+      const scope = nock('https://api.github.com:443')
+         .get('/repos/octo/release-notes/contents/docs/release%23notes.md')
+         .query({ref: 'release-2026'})
+         .reply(200, {sha: 'content-sha'});
+      return repository.getContents('release-2026', 'docs/release#notes.md').then(function() {
+         scope.done();
+      });
+   });
+
+   it('should encode reserved characters when getting a SHA', function() {
+      const scope = nock('https://api.github.com:443')
+         .get('/repos/octo/release-notes/contents/reports/draft%3F.txt')
+         .query({ref: 'release-2026'})
+         .reply(200, {sha: 'content-sha'});
+      return repository.getSha('release-2026', 'reports/draft?.txt').then(function() {
+         scope.done();
+      });
+   });
+
+   it('should encode reserved characters when writing a file', function() {
+      const scope = nock('https://api.github.com:443')
+         .get('/repos/octo/release-notes/contents/reports/draft%3F.txt')
+         .query({ref: 'release-2026'})
+         .reply(200, {sha: 'content-sha'})
+         .put('/repos/octo/release-notes/contents/reports/draft%3F.txt')
+         .reply(200, {commit: {sha: 'updated'}});
+      return repository.writeFile('release-2026', 'reports/draft?.txt', 'Draft', 'Update draft').then(function() {
+         scope.done();
+      });
+   });
+
+   it('should encode reserved characters when deleting a file', function() {
+      const scope = nock('https://api.github.com:443')
+         .get('/repos/octo/release-notes/contents/docs/release%23notes.md')
+         .query({ref: 'release-2026'})
+         .reply(200, {sha: 'content-sha'})
+         .delete('/repos/octo/release-notes/contents/docs/release%23notes.md')
+         .reply(200, {commit: {sha: 'deleted'}});
+      return repository.deleteFile('release-2026', 'docs/release#notes.md').then(function() {
+         scope.done();
+      });
+   });
+});