diff --git a/lib/tasks/import/api.js b/lib/tasks/import/api.js
index 3b5d8095f..e93be173a 100644
--- a/lib/tasks/import/api.js
+++ b/lib/tasks/import/api.js
@@ -39,53 +39,81 @@ async function setup(version, url, data) {
     await got.post('/authentication/setup/', {baseUrl, body, json: true});
 }
 
+function handleError(error) {
+    const {response} = error;
+    if (response.statusCode === 404) {
+        throw new SystemError({
+            message: 'There is no user with that email address.',
+            err: error
+        });
+    }
+
+    if (response.statusCode === 422) {
+        throw new SystemError({
+            message: 'Your password is incorrect.',
+            err: error
+        });
+    }
+
+    throw error;
+}
+
 async function getAuthOpts(version, url, {username, password}) {
     const baseUrl = getBaseUrl(version, url);
 
     if (semver.major(version) === 1) {
         const {body: configBody} = await got('/configuration/', {baseUrl, json: true});
         const {clientId, clientSecret} = get(configBody, 'configuration[0]', {});
-        const {body: authBody} = await got.post('/authentication/token/', {
+
+        try {
+            const {body: authBody} = await got.post('/authentication/token/', {
+                baseUrl,
+                json: true,
+                form: true,
+                body: {
+                    grant_type: 'password',
+                    client_id: clientId,
+                    client_secret: clientSecret,
+                    username,
+                    password
+                }
+            });
+
+            return {
+                baseUrl,
+                headers: {
+                    Authorization: `Bearer ${authBody.access_token}`
+                }
+            };
+        } catch (error) {
+            handleError(error);
+        }
+    }
+
+    try {
+        const {headers} = await got.post('/session/', {
             baseUrl,
-            json: true,
-            form: true,
-            body: {
-                grant_type: 'password',
-                client_id: clientId,
-                client_secret: clientSecret,
-                username,
-                password
-            }
+            headers: {
+                Origin: url,
+                'Content-Type': 'application/json'
+            },
+            body: JSON.stringify({username, password})
         });
 
+        /* istanbul ignore next */
+        const cookies = headers['set-cookie'] || [];
+        const filteredCookies = cookies.map(Cookie.parse).filter(Boolean).map(c => c.cookieString());
+
         return {
             baseUrl,
             headers: {
-                Authorization: `Bearer ${authBody.access_token}`
+                Origin: url,
+                Cookie: filteredCookies
             }
         };
+    } catch (error) {
+        handleError(error);
     }
-
-    const {headers} = await got.post('/session/', {
-        baseUrl,
-        headers: {
-            Origin: url,
-            'Content-Type': 'application/json'
-        },
-        body: JSON.stringify({username, password})
-    });
-
-    /* istanbul ignore next */
-    const cookies = headers['set-cookie'] || [];
-    const filteredCookies = cookies.map(Cookie.parse).filter(Boolean).map(c => c.cookieString());
-
-    return {
-        baseUrl,
-        headers: {
-            Origin: url,
-            Cookie: filteredCookies
-        }
-    };
 }
 
 async function runImport(version, url, auth, exportFile) {
diff --git a/test/unit/tasks/import/api-spec.js b/test/unit/tasks/import/api-spec.js
index 632f541e7..7a371ca32 100644
--- a/test/unit/tasks/import/api-spec.js
+++ b/test/unit/tasks/import/api-spec.js
@@ -111,6 +111,54 @@ describe('Unit > Tasks > Import > setup', function () {
             expect(importScope.isDone()).to.be.true;
         });
 
+        it('handles 404 auth error', async function () {
+            const clientId = 'client-id';
+            const clientSecret = 'client-secret';
+            const configBody = {
+                configuration: [{
+                    clientId, clientSecret
+                }]
+            };
+
+            const tokenRequestBody = {
+                grant_type: 'password',
+                client_id: clientId,
+                client_secret: clientSecret,
+                username: 'test@example.com',
+                password: 'password'
+            };
+
+            const configScope = nock(testUrl)
+                .get('/ghost/api/v0.1/configuration/')
+                .reply(200, configBody);
+
+            const tokenScope = nock(testUrl)
+                .post('/ghost/api/v0.1/authentication/token/', tokenRequestBody)
+                .reply(404, {});
+
+            const importScope = nock(testUrl, {
+                reqheaders: {
+                    Authorization: 'Bearer access-token'
+                }
+            }).post('/ghost/api/v0.1/db/').reply(200, {});
+
+            try {
+                await runImport('1.0.0', testUrl, {
+                    username: 'test@example.com',
+                    password: 'password'
+                }, path.join(__dirname, 'fixtures/0.11.x.json'));
+            } catch (error) {
+                expect(error).to.be.an.instanceof(SystemError);
+                expect(error.message).to.equal('There is no user with that email address.');
+                expect(configScope.isDone()).to.be.true;
+                expect(tokenScope.isDone()).to.be.true;
+                expect(importScope.isDone()).to.be.false;
+                return;
+            }
+
+            expect.fail('runImport should have errored');
+        });
+
         it('2.x', async function () {
             const sessionScope = nock(testUrl, {
                 reqheaders: {
@@ -141,6 +189,41 @@ describe('Unit > Tasks > Import > setup', function () {
             expect(importScope.isDone()).to.be.true;
         });
 
+        it('handles 422 auth error', async function () {
+            const sessionScope = nock(testUrl, {
+                reqheaders: {
+                    Origin: testUrl
+                }
+            }).post('/ghost/api/v2/admin/session/', {
+                username: 'test@example.com',
+                password: 'password'
+            }).reply(422, 'Error');
+
+            const importScope = nock(testUrl, {
+                reqheaders: {
+                    cookie: [
+                        'ghost-admin-api-session=test-session-data'
+                    ],
+                    origin: testUrl
+                }
+            }).post('/ghost/api/v2/admin/db/').reply(201, {});
+
+            try {
+                await runImport('2.0.0', 'http://localhost:2368', {
+                    username: 'test@example.com',
+                    password: 'password'
+                }, path.join(__dirname, 'fixtures/2.x.json'));
+            } catch (error) {
+                expect(error).to.be.an.instanceof(SystemError);
+                expect(error.message).to.equal('Your password is incorrect.');
+                expect(sessionScope.isDone()).to.be.true;
+                expect(importScope.isDone()).to.be.false;
+                return;
+            }
+
+            expect.fail('runImport should have errored');
+        });
+
         it('3.x', async function () {
             const sessionScope = nock(testUrl, {
                 reqheaders: {
@@ -170,6 +253,41 @@ describe('Unit > Tasks > Import > setup', function () {
             expect(sessionScope.isDone()).to.be.true;
             expect(importScope.isDone()).to.be.true;
         });
+
+        it('rethrows non-auth errors', async function () {
+            const sessionScope = nock(testUrl, {
+                reqheaders: {
+                    Origin: testUrl
+                }
+            }).post('/ghost/api/v3/admin/session/', {
+                username: 'test@example.com',
+                password: 'password'
+            }).reply(500, 'Error');
+
+            const importScope = nock(testUrl, {
+                reqheaders: {
+                    cookie: [
+                        'ghost-admin-api-session=test-session-data'
+                    ],
+                    origin: testUrl
+                }
+            }).post('/ghost/api/v3/admin/db/').reply(201, {});
+
+            try {
+                await runImport('3.0.0', 'http://localhost:2368', {
+                    username: 'test@example.com',
+                    password: 'password'
+                }, path.join(__dirname, 'fixtures/3.x.json'));
+            } catch (error) {
+                expect(error.response).to.exist;
+                expect(error.response.statusCode).to.equal(500);
+                expect(sessionScope.isDone()).to.be.true;
+                expect(importScope.isDone()).to.be.false;
+                return;
+            }
+
+            expect.fail('runImport should have errored');
+        });
     });
 
     describe('downloadExport', function () {