diff --git a/.changes/next-release/bugfix-213273c1-12a5-47d1-b973-499d25e1d68e.json b/.changes/next-release/bugfix-213273c1-12a5-47d1-b973-499d25e1d68e.json
new file mode 100644
index 00000000000..a35b78228d3
--- /dev/null
+++ b/.changes/next-release/bugfix-213273c1-12a5-47d1-b973-499d25e1d68e.json
@@ -0,0 +1,4 @@
+{
+  "type" : "bugfix",
+  "description" : "Fix issue where users are unable to login to Amazon Q if they have previously authenticated (#5214)"
+}
\ No newline at end of file
diff --git a/plugins/core/jetbrains-community/src/software/aws/toolkits/jetbrains/core/credentials/ToolkitConnectionImpls.kt b/plugins/core/jetbrains-community/src/software/aws/toolkits/jetbrains/core/credentials/ToolkitConnectionImpls.kt
index fb89054b5f2..f7c85b05e6c 100644
--- a/plugins/core/jetbrains-community/src/software/aws/toolkits/jetbrains/core/credentials/ToolkitConnectionImpls.kt
+++ b/plugins/core/jetbrains-community/src/software/aws/toolkits/jetbrains/core/credentials/ToolkitConnectionImpls.kt
@@ -3,6 +3,7 @@
 
 package software.aws.toolkits.jetbrains.core.credentials
 
+import com.fasterxml.jackson.annotation.JsonIgnore
 import com.intellij.openapi.Disposable
 import com.intellij.openapi.util.Disposer
 import software.aws.toolkits.core.TokenConnectionSettings
@@ -73,6 +74,7 @@ sealed class ManagedBearerSsoConnection(
             region
         )
 
+    @JsonIgnore
     override fun getConnectionSettings(): TokenConnectionSettings = provider
 
     override fun dispose() {
@@ -99,6 +101,7 @@ class DetectedDiskSsoSessionConnection(
             region
         )
 
+    @JsonIgnore
     override fun getConnectionSettings(): TokenConnectionSettings = provider
 
     override fun dispose() {
diff --git a/plugins/core/jetbrains-community/tst/software/aws/toolkits/jetbrains/core/credentials/DefaultToolkitAuthManagerTest.kt b/plugins/core/jetbrains-community/tst/software/aws/toolkits/jetbrains/core/credentials/DefaultToolkitAuthManagerTest.kt
index 3f5d4962438..f63be201d7c 100644
--- a/plugins/core/jetbrains-community/tst/software/aws/toolkits/jetbrains/core/credentials/DefaultToolkitAuthManagerTest.kt
+++ b/plugins/core/jetbrains-community/tst/software/aws/toolkits/jetbrains/core/credentials/DefaultToolkitAuthManagerTest.kt
@@ -3,6 +3,7 @@
 
 package software.aws.toolkits.jetbrains.core.credentials
 
+import com.fasterxml.jackson.module.kotlin.jacksonObjectMapper
 import com.intellij.openapi.Disposable
 import com.intellij.openapi.application.ApplicationManager
 import com.intellij.testFramework.ProjectExtension
@@ -453,6 +454,22 @@ class DefaultToolkitAuthManagerTest {
         }
     }
 
+    @Test
+    fun `serializing LegacyManagedBearerSsoConnection does not include connectionSettings`() {
+        val profile = ManagedSsoProfile("us-east-1", "startUrl000", listOf("scopes"))
+        val connection = sut.createConnection(profile) as LegacyManagedBearerSsoConnection
+
+        assertThat(jacksonObjectMapper().writeValueAsString(connection)).doesNotContain("connectionSettings")
+    }
+
+    @Test
+    fun `serializing ProfileSsoManagedBearerSsoConnection does not include connectionSettings`() {
+        val profile = UserConfigSsoSessionProfile("sessionName", "us-east-1", "startUrl000", listOf("scopes"))
+        val connection = sut.createConnection(profile) as ProfileSsoManagedBearerSsoConnection
+
+        assertThat(jacksonObjectMapper().writeValueAsString(connection)).doesNotContain("connectionSettings")
+    }
+
     private companion object {
         @ExtendWith(ProjectExtension::class)
         val projectRule = ProjectRule()