diff --git a/packages/cli/src/commands/versions/bump.test.ts b/packages/cli/src/commands/versions/bump.test.ts
index ae1a4c4627..a5c867fccd 100644
--- a/packages/cli/src/commands/versions/bump.test.ts
+++ b/packages/cli/src/commands/versions/bump.test.ts
@@ -20,8 +20,9 @@ import { Command } from 'commander';
 import { resolve as resolvePath } from 'path';
 import { paths } from '../../lib/paths';
 import * as runObj from '../../lib/run';
-import bump, { bumpBackstageJsonVersion } from './bump';
+import bump, { bumpBackstageJsonVersion, createVersionFinder } from './bump';
 import { withLogCollector } from '@backstage/test-utils';
+import { YarnInfoInspectData } from '../../lib/versioning/packages';
 
 // Remove log coloring to simplify log matching
 jest.mock('chalk', () => ({
@@ -442,3 +443,92 @@ describe('bumpBackstageJsonVersion', () => {
     expect(json).toEqual({ version: '1.4.1' });
   });
 });
+
+describe('createVersionFinder', () => {
+  async function findVersion(tag: string, data: Partial<YarnInfoInspectData>) {
+    const fetcher = () =>
+      Promise.resolve({
+        name: '@backstage/core',
+        'dist-tags': {},
+        versions: [],
+        time: {},
+        ...data,
+      });
+
+    const versionFinder = createVersionFinder(tag, fetcher);
+    let result;
+    await withLogCollector(async () => {
+      result = await versionFinder('@backstage/core');
+    });
+    return result;
+  }
+
+  it('should create version finder', async () => {
+    await expect(
+      findVersion('latest', {
+        time: { '1.0.0': '2020-01-01T00:00:00.000Z' },
+        'dist-tags': { latest: '1.0.0' },
+      }),
+    ).resolves.toBe('1.0.0');
+
+    await expect(
+      findVersion('main', {
+        time: { '1.0.0': '2020-01-01T00:00:00.000Z' },
+        'dist-tags': { latest: '1.0.0' },
+      }),
+    ).resolves.toBe('1.0.0');
+
+    await expect(
+      findVersion('next', {
+        time: { '1.0.0': '2020-01-01T00:00:00.000Z' },
+        'dist-tags': { latest: '1.0.0' },
+      }),
+    ).resolves.toBe('1.0.0');
+
+    await expect(
+      findVersion('next', {
+        time: {
+          '1.0.0': '2020-01-01T00:00:00.000Z',
+          '0.9.0': '2010-01-01T00:00:00.000Z',
+        },
+        'dist-tags': { latest: '1.0.0', next: '0.9.0' },
+      }),
+    ).resolves.toBe('1.0.0');
+
+    await expect(
+      findVersion('next', {
+        time: {
+          '1.0.0': '2020-01-01T00:00:00.000Z',
+          '0.9.0': '2020-02-01T00:00:00.000Z',
+        },
+        'dist-tags': { latest: '1.0.0', next: '0.9.0' },
+      }),
+    ).resolves.toBe('0.9.0');
+
+    await expect(findVersion('next', {})).rejects.toThrow(
+      "No target 'latest' version found for @backstage/core",
+    );
+
+    await expect(
+      findVersion('next', {
+        time: {
+          '0.9.0': '2020-02-01T00:00:00.000Z',
+        },
+        'dist-tags': { latest: '1.0.0', next: '0.9.0' },
+      }),
+    ).rejects.toThrow(
+      "No time available for version '1.0.0' of @backstage/core",
+    );
+
+    await expect(
+      findVersion('next', {
+        time: {
+          '1.0.0': '2020-01-01T00:00:00.000Z',
+        },
+        'dist-tags': { latest: '1.0.0', next: '0.9.0' },
+      }),
+    ).rejects.toThrow(
+      "No time available for version '0.9.0' of @backstage/core",
+    );
+  });
+});
diff --git a/packages/cli/src/commands/versions/bump.ts b/packages/cli/src/commands/versions/bump.ts
index 2371011be3..af188cd472 100644
--- a/packages/cli/src/commands/versions/bump.ts
+++ b/packages/cli/src/commands/versions/bump.ts
@@ -284,7 +284,10 @@ export default async (cmd: Command) => {
   }
 };
 
-function createVersionFinder(releaseLine = 'latest') {
+export function createVersionFinder(
+  releaseLine = 'latest',
+  packageInfoFetcher = fetchPackageInfo,
+) {
   // The main release line is just an alias for latest
   const distTag = releaseLine === 'main' ? 'latest' : releaseLine;
   const found = new Map<string, string>();
@@ -296,26 +299,35 @@ function createVersionFinder(releaseLine = 'latest') {
     }
 
     console.log(`Checking for updates of ${name}`);
-    const info = await fetchPackageInfo(name);
+    const info = await packageInfoFetcher(name);
     const latestVersion = info['dist-tags'].latest;
     if (!latestVersion) {
       throw new Error(`No target 'latest' version found for ${name}`);
     }
-    if (distTag === 'latest') {
-      found.set(name, latestVersion);
-      return latestVersion;
-    }
+
     const taggedVersion = info['dist-tags'][distTag];
-    if (!taggedVersion) {
+    if (distTag === 'latest' || !taggedVersion) {
       found.set(name, latestVersion);
       return latestVersion;
     }
-    const latestVersionRelease = new Date(info.time[latestVersion]);
-    const taggedVersionRelease = new Date(info.time[taggedVersion]);
-    if (latestVersionRelease > taggedVersionRelease) {
-      console.log(
-        `using 'latest' dist tag for ${name} as its newer than '${distTag}'`,
+
+    const latestVersionDateStr = info.time[latestVersion];
+    const taggedVersionDateStr = info.time[taggedVersion];
+    if (!latestVersionDateStr) {
+      throw new Error(
+        `No time available for version '${latestVersion}' of ${name}`,
       );
+    }
+    if (!taggedVersionDateStr) {
+      throw new Error(
+        `No time available for version '${taggedVersion}' of ${name}`,
+      );
+    }
+
+    const latestVersionRelease = new Date(latestVersionDateStr).getTime();
+    const taggedVersionRelease = new Date(taggedVersionDateStr).getTime();
+    if (latestVersionRelease > taggedVersionRelease) {
+      // Prefer latest version if it's newer.
       found.set(name, latestVersion);
       return latestVersion;
     }