diff --git a/cli/src/main/java/com/okta/cli/OktaCli.java b/cli/src/main/java/com/okta/cli/OktaCli.java
index dd4c2c29..b39e539c 100644
--- a/cli/src/main/java/com/okta/cli/OktaCli.java
+++ b/cli/src/main/java/com/okta/cli/OktaCli.java
@@ -44,6 +44,8 @@
                 AutoComplete.GenerateCompletion.class})
 public class OktaCli implements Runnable {
 
+    public static final String VERSION = ApplicationInfo.get().get("okta-cli");
+
     @Spec
     private CommandSpec spec;
 
@@ -150,8 +152,7 @@ public static class VersionProvider implements CommandLine.IVersionProvider {
 
         @Override
         public String[] getVersion() throws Exception {
-            String version = ApplicationInfo.get().get("okta-cli");
-            return new String[] {version };
+            return new String[] { VERSION };
         }
     }
 }
diff --git a/cli/src/main/java/com/okta/cli/commands/BaseCommand.java b/cli/src/main/java/com/okta/cli/commands/BaseCommand.java
index 9dbd62b6..e1639a07 100644
--- a/cli/src/main/java/com/okta/cli/commands/BaseCommand.java
+++ b/cli/src/main/java/com/okta/cli/commands/BaseCommand.java
@@ -17,20 +17,44 @@
 
 import com.okta.cli.Environment;
 import com.okta.cli.OktaCli;
+import com.okta.cli.common.model.Semver;
+import com.okta.cli.common.model.VersionInfo;
+import com.okta.cli.common.service.DefaultStartRestClient;
+import com.okta.cli.common.service.StartRestClient;
 import com.okta.cli.console.ConsoleOutput;
 import com.okta.cli.console.Prompter;
 import picocli.CommandLine;
 
+import java.util.Optional;
 import java.util.concurrent.Callable;
+import java.util.concurrent.ExecutionException;
+import java.util.concurrent.Executors;
+import java.util.concurrent.Future;
+import java.util.concurrent.TimeUnit;
+import java.util.concurrent.TimeoutException;
 
 public abstract class BaseCommand implements Callable<Integer> {
 
     @CommandLine.Mixin
     private OktaCli.StandardOptions standardOptions;
 
-    public BaseCommand() {}
+    private final StartRestClient restClient;
+
+    public BaseCommand() {
+        this(new DefaultStartRestClient());
+    }
+
+    BaseCommand(StartRestClient restClient) {
+        this.restClient = restClient;
+    }
 
     public BaseCommand(OktaCli.StandardOptions standardOptions) {
+        this();
+        this.standardOptions = standardOptions;
+    }
+
+    BaseCommand(StartRestClient restClient, OktaCli.StandardOptions standardOptions) {
+        this(restClient);
         this.standardOptions = standardOptions;
     }
 
@@ -38,7 +62,17 @@ public BaseCommand(OktaCli.StandardOptions standardOptions) {
 
     @Override
     public Integer call() throws Exception {
-        return runCommand();
+
+        // Before running the command, kick off a thread to get the latest version
+        Semver currentVersion = getCurrentVersion();
+        Future<Optional<VersionInfo>> future = asyncVersionInfo(currentVersion);
+
+        // run the actual command
+        int exitCode = runCommand();
+
+        // After the command finishes alert the user if needed
+        handleVersionInfo(future, currentVersion);
+        return exitCode;
     }
 
     protected OktaCli.StandardOptions getStandardOptions() {
@@ -56,4 +90,45 @@ protected Prompter getPrompter() {
     protected Environment getEnvironment() {
         return standardOptions.getEnvironment();
     }
+
+    private Future<Optional<VersionInfo>> asyncVersionInfo(Semver currentVersion) {
+
+        Callable<Optional<VersionInfo>> versionInfoCallable = () -> {
+            // if the shell is NOT interactive skip the version check, it's being used in a script
+            if (currentVersion.isReleaseBuild() && standardOptions.getEnvironment().isInteractive()) {
+                return Optional.of(restClient.getVersionInfo());
+            } else {
+                return Optional.empty();
+            }
+        };
+        return Executors.newSingleThreadExecutor().submit(versionInfoCallable);
+    }
+
+    // protected to allow for testing
+    Semver getCurrentVersion() {
+        return Semver.parse(OktaCli.VERSION);
+    }
+
+    private void handleVersionInfo(Future<Optional<VersionInfo>> future, Semver currentVersion) {
+
+        try {
+            future.get(2, TimeUnit.SECONDS)
+                .ifPresent(info -> {
+                    if (Semver.parse(info.getLatestVersion()).isGreaterThan(currentVersion)) {
+                        ConsoleOutput out = getConsoleOutput();
+                        out.writeLine("");
+                        out.bold("A new version of the Okta CLI is available: " + info.getLatestVersion());
+                        out.writeLine("");
+                        getConsoleOutput().bold("See what's new: " + info.getLatestReleaseUrl());
+                        out.writeLine("");
+                    }
+                });
+        } catch (InterruptedException | ExecutionException | TimeoutException e) {
+            // by default do NOT show any errors from fetching the version
+            if (standardOptions.isVerbose()) {
+                getConsoleOutput().writeError("Failed to fetch latest CLI Version:");
+                e.printStackTrace();
+            }
+        }
+    }
 }
diff --git a/cli/src/test/groovy/com/okta/cli/commands/BaseCommandTest.groovy b/cli/src/test/groovy/com/okta/cli/commands/BaseCommandTest.groovy
new file mode 100644
index 00000000..3a0fe34d
--- /dev/null
+++ b/cli/src/test/groovy/com/okta/cli/commands/BaseCommandTest.groovy
@@ -0,0 +1,117 @@
+/*
+ * Copyright 2020-Present Okta, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package com.okta.cli.commands
+
+import com.okta.cli.OktaCli
+import com.okta.cli.common.model.Semver
+import com.okta.cli.common.model.VersionInfo
+import com.okta.cli.common.service.StartRestClient
+import com.okta.cli.console.ConsoleOutput
+import org.mockito.invocation.InvocationOnMock
+import org.mockito.stubbing.Answer
+import org.testng.annotations.Test
+
+import java.time.Duration
+
+import static org.hamcrest.MatcherAssert.assertThat
+import static org.hamcrest.Matchers.containsString
+import static org.hamcrest.Matchers.emptyString
+import static org.mockito.Mockito.mock
+import static org.mockito.Mockito.when
+
+class BaseCommandTest {
+
+    @Test
+    void notifyNewVersionTest() {
+
+        def baos = new ByteArrayOutputStream()
+
+        def command = new StubCommand(baos)
+        command.call()
+
+        def output = baos.toString()
+        assertThat output, containsString("A new version of the Okta CLI is available: 1.2.3")
+        assertThat output, containsString("See what's new: https://example.com/release/1.2.3")
+    }
+
+    @Test
+    void failVersionFetch() {
+
+        def baos = new ByteArrayOutputStream()
+        def restClient = mock(StartRestClient)
+        when(restClient.getVersionInfo()).thenThrow(new RuntimeException("expected test exception"))
+
+        def command = new StubCommand(baos, restClient)
+        command.call()
+
+        def output = baos.toString()
+        assertThat output, emptyString()
+    }
+
+    @Test(timeOut = 4000l)
+    void versionTimeout() {
+
+        def baos = new ByteArrayOutputStream()
+        def restClient = mock(StartRestClient)
+        when(restClient.getVersionInfo()).thenThrow(new RuntimeException("expected test exception"))
+
+        def command = new StubCommand(baos, StubCommand.mockRestClient("1.2.3", Duration.ofSeconds(3)))
+        command.call()
+
+        def output = baos.toString()
+        assertThat "Expected version thread to timeout, the result is no version info is displayed to the user", output, emptyString()
+    }
+
+    static class StubCommand extends BaseCommand {
+
+        private final int exitCode
+        private final String currentVersion
+
+        StubCommand(ByteArrayOutputStream baos, StartRestClient restClient = mockRestClient("1.2.3", Duration.ofMillis(0)), OktaCli.StandardOptions standardOptions = new OktaCli.StandardOptions(), int exitCode = 0, String currentVersion = "1.0.1") {
+            super(restClient, standardOptions)
+            this.exitCode = exitCode
+            this.currentVersion = currentVersion
+
+            PrintStream printStream = new PrintStream(baos)
+            ConsoleOutput out = new ConsoleOutput.AnsiConsoleOutput(printStream, false)
+            getEnvironment().consoleOutput = out
+        }
+
+        @Override
+        protected int runCommand() throws Exception {
+            return exitCode
+        }
+
+        @Override
+        Semver getCurrentVersion() {
+            return Semver.parse(currentVersion)
+        }
+
+        static StartRestClient mockRestClient(String version, Duration delay) {
+            def restClient = mock(StartRestClient)
+            when(restClient.getVersionInfo()).thenAnswer(new Answer<VersionInfo>() {
+                @Override
+                VersionInfo answer(InvocationOnMock invocation) throws Throwable {
+                    Thread.sleep(delay.toMillis())
+                    return new VersionInfo()
+                            .setLatestVersion(version)
+                            .setLatestReleaseUrl("https://example.com/release/${version}")
+                }
+            })
+            return restClient
+        }
+    }
+}
\ No newline at end of file
diff --git a/common/src/main/java/com/okta/cli/common/model/Semver.java b/common/src/main/java/com/okta/cli/common/model/Semver.java
new file mode 100644
index 00000000..08062e2c
--- /dev/null
+++ b/common/src/main/java/com/okta/cli/common/model/Semver.java
@@ -0,0 +1,115 @@
+/*
+ * Copyright 2020-Present Okta, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package com.okta.cli.common.model;
+
+import lombok.Data;
+
+import java.util.Comparator;
+
+/**
+ * A basic Semver class that represents a typical Maven style version {@code MAJOR.MINOR.PATCH[-SNAPSHOT][-QUALIFIER]} that is
+ * mapped to a Semver, where the optional {@code [-SNAPSHOT][-QUALIFIER]} is considered buildMetadata.
+ *
+ * This distinction is subtle, but _true_ semver is {@code MAJOR.MINOR.PATCH[-pre-release][+buildMetadata]}, the differences is the '{@code +}'.
+ */
+@Data
+public class Semver implements Comparable<Semver> {
+
+    private final String version;
+
+    private final Integer major;
+    private final Integer minor;
+    private final Integer patch;
+    private final String buildMetadata;
+    private final boolean releaseBuild;
+
+   private Semver(String version, Integer major, Integer minor, Integer patch, String buildMetadata, boolean releaseBuild) {
+        this.version = version;
+        this.major = major;
+        this.minor = minor;
+        this.patch = patch;
+        this.buildMetadata = buildMetadata;
+        this.releaseBuild = releaseBuild;
+    }
+
+    @Override
+    public int compareTo(Semver other) {
+        return Comparator.comparing(Semver::getMajor, Comparator.nullsLast(Comparator.naturalOrder()))
+                .thenComparing(Semver::getMinor, Comparator.nullsLast(Comparator.naturalOrder()))
+                .thenComparing(Semver::getPatch, Comparator.nullsLast(Comparator.naturalOrder()))
+                .thenComparing(Semver::isReleaseBuild, Comparator.nullsLast(Comparator.naturalOrder()))
+                .thenComparing(Semver::getVersion, Comparator.nullsLast(Comparator.naturalOrder()))
+                .compare(this, other);
+    }
+
+    public boolean isGreaterThan(String otherVersion) {
+        return this.isGreaterThan(Semver.parse(otherVersion));
+    }
+
+    public boolean isGreaterThan(Semver other) {
+        return this.compareTo(other) > 0;
+    }
+
+    public static Semver parse(String version) {
+
+        // overly simple semver parser, split on '.', then grab the optional '-qualifier' from the last segment
+        // Using the "official" semver regex works, but it has a risk of a REDOS attack, i.e. it's really slow
+        String[] parts = version.split("\\.", 3);
+        String major = null;
+        String minor = null;
+        String patch = null;
+        boolean release = true;
+        String meta = null;
+
+        if (parts.length > 0) {
+            // split on the qualifier i.e. 1.2.[3-gitSha], or 1.2.3-SNAPSHOT-gitSha
+            String[] lastAndQual = parts[parts.length - 1].split("-", 2);
+
+            // qualifier
+            if (lastAndQual.length == 2) {
+                meta = lastAndQual[1];
+            }
+
+            // update the last part to just the simple value without the qualifier
+            parts[parts.length - 1] = lastAndQual[0];
+
+            major = parts[0];
+            if (parts.length > 1) {
+                minor = parts[1];
+            }
+
+            if (parts.length > 2) {
+                patch = parts[2];
+            }
+
+            if (version.contains("-SNAPSHOT")) {
+                release = false;
+            }
+        }
+        return new Semver(version, toInt(major), toInt(minor), toInt(patch), meta, release);
+    }
+
+    private static Integer toInt(String value) {
+        if (value == null) {
+            return null;
+        }
+        try {
+            return Integer.parseInt(value);
+        } catch (NumberFormatException e) {
+            return null;
+        }
+    }
+}
diff --git a/common/src/test/groovy/com/okta/cli/common/model/SemverTest.groovy b/common/src/test/groovy/com/okta/cli/common/model/SemverTest.groovy
new file mode 100644
index 00000000..28dee598
--- /dev/null
+++ b/common/src/test/groovy/com/okta/cli/common/model/SemverTest.groovy
@@ -0,0 +1,80 @@
+/*
+ * Copyright 2020-Present Okta, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+package com.okta.cli.common.model
+
+import org.testng.annotations.DataProvider
+import org.testng.annotations.Test
+
+import static org.hamcrest.MatcherAssert.assertThat
+import static org.hamcrest.Matchers.equalTo
+
+class SemverTest {
+
+    @Test
+    void parseTest() {
+        // equals method generated by lombok
+        assertThat Semver.parse("1"), equalTo(new Semver("1", 1, null, null, null, true))
+        assertThat Semver.parse("1.2"), equalTo(new Semver("1.2", 1, 2, null, null, true))
+        assertThat Semver.parse("1.0.3"), equalTo(new Semver("1.0.3", 1, 0, 3, null, true))
+        assertThat Semver.parse("1.0.3-SNAPSHOT"), equalTo(new Semver("1.0.3-SNAPSHOT", 1, 0, 3, "SNAPSHOT", false))
+        assertThat Semver.parse("1.0.3-SNAPSHOT-foo"), equalTo(new Semver("1.0.3-SNAPSHOT-foo", 1, 0, 3, "SNAPSHOT-foo", false))
+        assertThat Semver.parse("0.10.14-qualifier-goes-here"), equalTo(new Semver("0.10.14-qualifier-goes-here", 0, 10, 14, "qualifier-goes-here", true))
+
+        assertThat Semver.parse("a.b.c"), equalTo(new Semver("a.b.c", null, null, null, null, true))
+    }
+
+    @Test(dataProvider = "greaterThan")
+    void greaterThanTest(String versionA, String versionB) {
+        assertGreaterThan versionA, versionB
+    }
+
+    @Test(dataProvider = "lessThanOrEqual")
+    void lessThanOrEqualDataTest(String versionA, String versionB) {
+        assertLessThanOrEqual versionA, versionB
+    }
+
+    private void assertLessThanOrEqual(String a, String b) {
+        assertThat "Expected version `${a}` to be less than or equal toversion '${b}'", !Semver.parse(a).isGreaterThan(b)
+    }
+
+    private void assertGreaterThan(String a, String b) {
+        assertThat "Expected version `${a}` to be greater than version '${b}'", Semver.parse(a).isGreaterThan(b)
+    }
+
+    @DataProvider(name = "greaterThan")
+    Object[][] greaterThanData() {
+        return [
+                ["1.2.3", "1.2.2"],
+                ["1.2.3", "1.2.3-SNAPSHOT"],
+                ["1.2.3", "0.2.2"],
+                ["2", "1.0"],
+                ["2.0", "1.0.0"],
+                ["10.0", "1.0.0"],
+                ["1.2.3", "0.2.2"],
+        ]
+    }
+
+    @DataProvider(name = "lessThanOrEqual")
+    Object[][] lessThanOrEqualData() {
+        return [
+                ["1.2.2", "1.2.3"],
+                ["1.0.0", "2"],
+                ["1.10.0", "2.2"],
+                ["1.2.3-SNAPSHOT", "1.2.3"],
+                ["0.2.2", "1.2.3"],
+        ]
+    }
+}