diff --git a/src/cli/commands/applications/remove.ts b/src/cli/commands/applications/remove.ts
index 0f5f389..9f39237 100644
--- a/src/cli/commands/applications/remove.ts
+++ b/src/cli/commands/applications/remove.ts
@@ -29,6 +29,7 @@ export function removeApplicationCommand(
         const { config, groupname, applicationpaths } = argv;
         const updatedConfig = await removeApplication({
           config: config.contents,
+          configPath: config.path,
           groupName: groupname,
           relativePaths: applicationpaths,
         });
diff --git a/src/core/applications/add.ts b/src/core/applications/add.ts
index 9340bbb..fe0e073 100644
--- a/src/core/applications/add.ts
+++ b/src/core/applications/add.ts
@@ -1,7 +1,12 @@
 import path from 'path';
 import fs from 'fs';
 
-import { emphasize, getGroupConfig, isNodeJSError } from '../utils';
+import {
+  emphasize,
+  getGroupConfig,
+  isNodeJSError,
+  normalizePaths,
+} from '../utils';
 import { VersionGuardConfig } from '../config';
 import { VersionGuardError } from '../errors';
 
@@ -44,20 +49,20 @@ export async function addApplications({
   config,
 }: AddApplicationOptions): Promise<VersionGuardConfig> {
   const groupConfig = getGroupConfig(groupName, config);
-  relativePaths.forEach(relativePath => {
+  const normalizedPaths = normalizePaths({ configPath, relativePaths });
+  normalizedPaths.forEach(relativePath => {
     if (groupConfig.applications.includes(relativePath)) {
       throw VersionGuardError.from(
         emphasize`Group ${groupName} already includes application with path ${relativePath}`,
       );
     }
   });
-  await ensurePackageJsonsExist(path.dirname(configPath), relativePaths);
-
+  await ensurePackageJsonsExist(path.dirname(configPath), normalizedPaths);
   return {
     ...config,
     [groupName]: {
       ...groupConfig,
-      applications: groupConfig.applications.concat(relativePaths),
+      applications: groupConfig.applications.concat(normalizedPaths),
     },
   };
 }
diff --git a/src/core/applications/remove.ts b/src/core/applications/remove.ts
index 17ed791..9068690 100644
--- a/src/core/applications/remove.ts
+++ b/src/core/applications/remove.ts
@@ -1,4 +1,4 @@
-import { emphasize, getGroupConfig } from '../utils';
+import { emphasize, getGroupConfig, normalizePaths } from '../utils';
 import { VersionGuardConfig } from '../config';
 import { VersionGuardError } from '../errors';
 
@@ -6,15 +6,18 @@ interface RemoveApplicationOptions {
   relativePaths: string[];
   groupName: string;
   config: VersionGuardConfig;
+  configPath: string;
 }
 
 export function removeApplication({
   relativePaths,
   config,
+  configPath,
   groupName,
 }: RemoveApplicationOptions): VersionGuardConfig {
   const groupConfig = getGroupConfig(groupName, config);
-  relativePaths.forEach(relativePath => {
+  const normalizedPaths = normalizePaths({ configPath, relativePaths });
+  normalizedPaths.forEach(relativePath => {
     if (!groupConfig.applications.includes(relativePath)) {
       throw VersionGuardError.from(
         emphasize`Group does not include application with path ${relativePath}`,
@@ -27,7 +30,7 @@ export function removeApplication({
     [groupName]: {
       ...groupConfig,
       applications: groupConfig.applications.filter(
-        path => !relativePaths.includes(path),
+        path => !normalizedPaths.includes(path),
       ),
     },
   };
diff --git a/src/core/utils.ts b/src/core/utils.ts
index 7298b41..f6d82ef 100644
--- a/src/core/utils.ts
+++ b/src/core/utils.ts
@@ -1,5 +1,6 @@
 import chalk from 'chalk';
-import semver, { SemVer } from 'semver';
+import semver from 'semver';
+import path from 'path';
 
 import { VersionGuardConfig } from './config';
 import { GroupConfig } from './groups';
@@ -76,3 +77,19 @@ export function getMinSemverVersionOrThrow(
   }
   return minVersion;
 }
+
+export function normalizePaths({
+  configPath,
+  relativePaths,
+}: {
+  configPath: string;
+  relativePaths: string[];
+}): string[] {
+  const configBase = path.dirname(configPath);
+  const paths = relativePaths.map(p =>
+    // combining `path.resolve` with `path.relative` in this way
+    // gets rid of any trailing slashes that may exist on `p`
+    path.relative(configBase, path.resolve(configBase, p)),
+  );
+  return paths;
+}