diff --git a/airbyte-webapp/src/components/connection/ConnectionStatus/useConnectionStatus.test.ts b/airbyte-webapp/src/components/connection/ConnectionStatus/useConnectionStatus.test.ts
index 6e10bd087b2..bcca2e827c4 100644
--- a/airbyte-webapp/src/components/connection/ConnectionStatus/useConnectionStatus.test.ts
+++ b/airbyte-webapp/src/components/connection/ConnectionStatus/useConnectionStatus.test.ts
@@ -255,26 +255,31 @@ describe("isHandleableScheduledConnection", () => {
 });
 
 describe("useConnectionStatus", () => {
-  /* Cases currently failing:
-  ${"most recent sync was successful, breaking schema changes"}                                       | ${ConnectionStatusIndicatorStatus.ActionRequired} | ${ConnectionStatus.inactive} | ${SchemaChange.breaking}     | ${ConnectionSyncStatus.ACTIVE}    | ${dayjs().subtract(1, "minute").unix()}  | ${undefined} | ${undefined}
-  ${"breaking schema changes, sync is outside of 2x frequency"}                                       | ${ConnectionStatusIndicatorStatus.ActionRequired} | ${ConnectionStatus.inactive} | ${SchemaChange.breaking}     | ${ConnectionSyncStatus.FAILED}    | ${dayjs().subtract(50, "hours").unix()}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
-  ${"last sync was cancelled, but last successful sync is within 2x frequency"}                       | ${ConnectionStatusIndicatorStatus.Late}           | ${ConnectionStatus.active}   | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.CANCELLED} | ${dayjs().subtract(50, "hours").unix()}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
-  */
+  const within1xFrequency = dayjs().subtract(20, "hours").unix();
+  const within2xFrequency = dayjs().subtract(28, "hours").unix();
+  const outside2xFrequency = dayjs().subtract(50, "hours").unix();
 
   it.each`
-    title                                                                                               | expectedConnectionStatus                     | connectionStatus           | schemaChange                 | connectionSyncStatus              | lastSuccessfulSync                       | scheduleType | scheduleData
-    ${"most recent sync was successful, no schema changes"}                                             | ${ConnectionStatusIndicatorStatus.OnTime}    | ${ConnectionStatus.active} | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.ACTIVE}    | ${dayjs().subtract(1, "minute").unix()}  | ${undefined} | ${undefined}
-    ${"new connection, not scheduled"}                                                                  | ${ConnectionStatusIndicatorStatus.Pending}   | ${ConnectionStatus.active} | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.EMPTY}     | ${undefined}                             | ${undefined} | ${undefined}
-    ${"new connection, scheduled"}                                                                      | ${ConnectionStatusIndicatorStatus.Pending}   | ${ConnectionStatus.active} | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.EMPTY}     | ${undefined}                             | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
-    ${"connection status is failed, no previous success"}                                               | ${ConnectionStatusIndicatorStatus.Error}     | ${ConnectionStatus.active} | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${undefined}                             | ${undefined} | ${undefined}
-    ${"connection status is failed, no previous success"}                                               | ${ConnectionStatusIndicatorStatus.OnTrack}   | ${ConnectionStatus.active} | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${dayjs().subtract(26, "hours").unix()}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
-    ${"connection status is failed, last previous success was within 2x schedule frequency"}            | ${ConnectionStatusIndicatorStatus.Error}     | ${ConnectionStatus.active} | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${dayjs().subtract(5, "minutes").unix()} | ${"cron"}    | ${{ cronExpression: "* * * * *", cronTimeZone: "UTC" }}
-    ${"connection status is failed, last previous success was a while ago, but cron is never late"}     | ${ConnectionStatusIndicatorStatus.Error}     | ${ConnectionStatus.active} | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${dayjs().subtract(50, "hours").unix()}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
-    ${"connection status is failed, last previous success was outside 2x schedule frequency"}           | ${ConnectionStatusIndicatorStatus.OnTrack}   | ${ConnectionStatus.active} | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.ACTIVE}    | ${dayjs().subtract(28, "hours").unix()}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
-    ${"last sync was successful, but the next sync hasn't started (within 2x frequency)"}               | ${ConnectionStatusIndicatorStatus.Late}      | ${ConnectionStatus.active} | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.ACTIVE}    | ${dayjs().subtract(52, "hours").unix()}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
-    ${"last sync was successful, but the next sync hasn't started (outside 2x frequency)"}              | ${ConnectionStatusIndicatorStatus.OnTime}    | ${ConnectionStatus.active} | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.ACTIVE}    | ${dayjs().subtract(52, "hours").unix()}  | ${"cron"}    | ${{ cronExpression: "* * * * *", cronTimeZone: "UTC" }}
-    ${"last sync was successful, but the next cron-scheduled sync hasn't started (cron is never late)"} | ${ConnectionStatusIndicatorStatus.Cancelled} | ${ConnectionStatus.active} | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.CANCELLED} | ${dayjs().subtract(2, "hours").unix()}   | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
-    ${"last sync was cancelled, but last successful sync is within 1x frequency"}                       | ${ConnectionStatusIndicatorStatus.Cancelled} | ${ConnectionStatus.active} | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.CANCELLED} | ${dayjs().subtract(2, "hours").unix()}   | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    title                                                                                           | expectedConnectionStatus                          | connectionStatus             | schemaChange                 | connectionSyncStatus              | lastSuccessfulSync    | scheduleType | scheduleData
+    ${"most recent sync was successful, no schema changes"}                                         | ${ConnectionStatusIndicatorStatus.OnTime}         | ${ConnectionStatus.active}   | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.ACTIVE}    | ${within1xFrequency}  | ${undefined} | ${undefined}
+    ${"most recent sync was successful, breaking schema changes"}                                   | ${ConnectionStatusIndicatorStatus.ActionRequired} | ${ConnectionStatus.inactive} | ${SchemaChange.breaking}     | ${ConnectionSyncStatus.ACTIVE}    | ${within1xFrequency}  | ${undefined} | ${undefined}
+    ${"breaking schema changes, sync is within 1x frequency"}                                       | ${ConnectionStatusIndicatorStatus.ActionRequired} | ${ConnectionStatus.inactive} | ${SchemaChange.breaking}     | ${ConnectionSyncStatus.FAILED}    | ${within1xFrequency}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"breaking schema changes, sync is within 2x frequency"}                                       | ${ConnectionStatusIndicatorStatus.ActionRequired} | ${ConnectionStatus.inactive} | ${SchemaChange.breaking}     | ${ConnectionSyncStatus.FAILED}    | ${within2xFrequency}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"breaking schema changes, sync is outside of 2x frequency"}                                   | ${ConnectionStatusIndicatorStatus.ActionRequired} | ${ConnectionStatus.inactive} | ${SchemaChange.breaking}     | ${ConnectionSyncStatus.FAILED}    | ${outside2xFrequency} | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"new connection, not scheduled"}                                                              | ${ConnectionStatusIndicatorStatus.Pending}        | ${ConnectionStatus.active}   | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.EMPTY}     | ${undefined}          | ${undefined} | ${undefined}
+    ${"new connection, scheduled"}                                                                  | ${ConnectionStatusIndicatorStatus.Pending}        | ${ConnectionStatus.active}   | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.EMPTY}     | ${undefined}          | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"connection status is failed, no previous success"}                                           | ${ConnectionStatusIndicatorStatus.Error}          | ${ConnectionStatus.active}   | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${undefined}          | ${undefined} | ${undefined}
+    ${"connection status is failed, last previous success was within 1x schedule frequency"}        | ${ConnectionStatusIndicatorStatus.OnTrack}        | ${ConnectionStatus.active}   | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${within1xFrequency}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"connection status is failed, last previous success was within 2x schedule frequency"}        | ${ConnectionStatusIndicatorStatus.OnTrack}        | ${ConnectionStatus.active}   | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${within2xFrequency}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"connection status is failed, last previous success was within 2x schedule frequency (cron)"} | ${ConnectionStatusIndicatorStatus.Error}          | ${ConnectionStatus.active}   | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${within2xFrequency}  | ${"cron"}    | ${{ cronExpression: "* * * * *", cronTimeZone: "UTC" }}
+    ${"connection status is failed, last previous success was outside 2x schedule frequency"}       | ${ConnectionStatusIndicatorStatus.Error}          | ${ConnectionStatus.active}   | ${SchemaChange.no_change}    | ${ConnectionSyncStatus.FAILED}    | ${outside2xFrequency} | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"connection status is failed, last previous success was within 2x schedule frequency"}        | ${ConnectionStatusIndicatorStatus.OnTrack}        | ${ConnectionStatus.active}   | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.ACTIVE}    | ${within2xFrequency}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"last sync was successful, but the next sync hasn't started (outside 2x frequency)"}          | ${ConnectionStatusIndicatorStatus.Late}           | ${ConnectionStatus.active}   | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.ACTIVE}    | ${outside2xFrequency} | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"last sync was successful, but the next sync hasn't started (outside 2x frequency, cron)"}    | ${ConnectionStatusIndicatorStatus.OnTime}         | ${ConnectionStatus.active}   | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.ACTIVE}    | ${outside2xFrequency} | ${"cron"}    | ${{ cronExpression: "* * * * *", cronTimeZone: "UTC" }}
+    ${"last sync was cancelled, but the next cron-scheduled sync hasn't started"}                   | ${ConnectionStatusIndicatorStatus.OnTime}         | ${ConnectionStatus.active}   | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.CANCELLED} | ${within1xFrequency}  | ${"cron"}    | ${{ cronExpression: "* * * * *", cronTimeZone: "UTC" }}
+    ${"last sync was cancelled, but last successful sync is within 1x frequency"}                   | ${ConnectionStatusIndicatorStatus.OnTime}         | ${ConnectionStatus.active}   | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.CANCELLED} | ${within1xFrequency}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"last sync was cancelled, but last successful sync is within 2x frequency"}                   | ${ConnectionStatusIndicatorStatus.OnTrack}        | ${ConnectionStatus.active}   | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.CANCELLED} | ${within2xFrequency}  | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
+    ${"last sync was cancelled, but last successful sync is outside 2x frequency"}                  | ${ConnectionStatusIndicatorStatus.Late}           | ${ConnectionStatus.active}   | ${SchemaChange.non_breaking} | ${ConnectionSyncStatus.CANCELLED} | ${outside2xFrequency} | ${"basic"}   | ${{ units: 24, timeUnit: "hours" }}
   `(
     "$title:" +
       "\n\treturns $expectedConnectionStatus when" +
diff --git a/airbyte-webapp/src/components/connection/ConnectionStatus/useConnectionStatus.ts b/airbyte-webapp/src/components/connection/ConnectionStatus/useConnectionStatus.ts
index 599694859b2..bc4070634ae 100644
--- a/airbyte-webapp/src/components/connection/ConnectionStatus/useConnectionStatus.ts
+++ b/airbyte-webapp/src/components/connection/ConnectionStatus/useConnectionStatus.ts
@@ -48,12 +48,15 @@ export const useConnectionStatus = () => {
   const lateMultiplier = useLateMultiplierExperiment();
   const errorMultiplier = useErrorMultiplierExperiment();
 
-  // Disabling the schema changes as it's the only actionable error and is per-connection, not stream
   const { connection } = useConnectionEditService();
   const { hasBreakingSchemaChange } = useSchemaChanges(connection.schemaChange);
 
   const { connectionEnabled, connectionStatus, lastSuccessfulSync } = useConnectionSyncContext();
 
+  if (hasBreakingSchemaChange) {
+    return ConnectionStatusIndicatorStatus.ActionRequired;
+  }
+
   if (!connectionEnabled) {
     return ConnectionStatusIndicatorStatus.Disabled;
   }
@@ -73,14 +76,6 @@ export const useConnectionStatus = () => {
     return ConnectionStatusIndicatorStatus.Error;
   }
 
-  if (hasBreakingSchemaChange && isConnectionLate(connection, lastSuccessfulSync, lateMultiplier)) {
-    return ConnectionStatusIndicatorStatus.ActionRequired;
-  }
-
-  if (connectionStatus === ConnectionSyncStatus.CANCELLED) {
-    return ConnectionStatusIndicatorStatus.Cancelled;
-  }
-
   // The `late` value is based on the `connection.streamCentricUI.late` experiment
   if (isConnectionLate(connection, lastSuccessfulSync, lateMultiplier)) {
     return ConnectionStatusIndicatorStatus.Late;
diff --git a/airbyte-webapp/src/components/connection/ConnectionStatusIndicator/ConnectionStatusIndicator.tsx b/airbyte-webapp/src/components/connection/ConnectionStatusIndicator/ConnectionStatusIndicator.tsx
index d48da97f3b0..73a5aa5216c 100644
--- a/airbyte-webapp/src/components/connection/ConnectionStatusIndicator/ConnectionStatusIndicator.tsx
+++ b/airbyte-webapp/src/components/connection/ConnectionStatusIndicator/ConnectionStatusIndicator.tsx
@@ -16,7 +16,6 @@ export enum ConnectionStatusIndicatorStatus {
   Error = "error",
   ActionRequired = "actionRequired",
   Disabled = "disabled",
-  Cancelled = "cancelled",
 }
 
 const ICON_BY_STATUS: Readonly<Record<ConnectionStatusIndicatorStatus, JSX.Element>> = {
@@ -27,7 +26,6 @@ const ICON_BY_STATUS: Readonly<Record<ConnectionStatusIndicatorStatus, JSX.Eleme
   pending: <ClockIcon />,
   late: <ClockIcon />,
   actionRequired: <Icon type="cross" withBackground />,
-  cancelled: <Icon type="minus" color="action" withBackground />,
 };
 
 const STYLE_BY_STATUS: Readonly<Record<ConnectionStatusIndicatorStatus, string>> = {
@@ -38,7 +36,6 @@ const STYLE_BY_STATUS: Readonly<Record<ConnectionStatusIndicatorStatus, string>>
   pending: styles["status--pending"],
   late: styles["status--late"],
   actionRequired: styles["status--actionRequired"],
-  cancelled: styles["status--cancelled"],
 };
 
 const BOX_STYLE_BY_STATUS: Readonly<Record<ConnectionStatusIndicatorStatus, string>> = {
@@ -49,7 +46,6 @@ const BOX_STYLE_BY_STATUS: Readonly<Record<ConnectionStatusIndicatorStatus, stri
   pending: styles["status--pending-withBox"],
   late: styles["status--late-withBox"],
   actionRequired: styles["status--actionRequired-withBox"],
-  cancelled: styles["status--cancelled-withBox"],
 };
 
 interface ConnectionStatusIndicatorProps {
diff --git a/airbyte-webapp/src/components/connection/ConnectionSync/ConnectionSyncContext.tsx b/airbyte-webapp/src/components/connection/ConnectionSync/ConnectionSyncContext.tsx
index 650a0f1cad6..5e001d8d22c 100644
--- a/airbyte-webapp/src/components/connection/ConnectionSync/ConnectionSyncContext.tsx
+++ b/airbyte-webapp/src/components/connection/ConnectionSync/ConnectionSyncContext.tsx
@@ -36,12 +36,7 @@ interface ConnectionSyncContext {
   lastSuccessfulSync?: number;
 }
 
-const jobStatusesIndicatingFinishedExecution: string[] = [
-  JobStatus.cancelled,
-  JobStatus.succeeded,
-  JobStatus.failed,
-  JobStatus.incomplete,
-];
+const jobStatusesIndicatingFinishedExecution: string[] = [JobStatus.succeeded, JobStatus.failed, JobStatus.incomplete];
 const useConnectionSyncContextInit = (jobs: JobWithAttemptsRead[]): ConnectionSyncContext => {
   const { connection } = useConnectionEditService();
   const [activeJob, setActiveJob] = useState(jobs[0]?.job);
diff --git a/airbyte-webapp/src/pages/connections/StreamStatusPage/ConnectionStatusOverview.tsx b/airbyte-webapp/src/pages/connections/StreamStatusPage/ConnectionStatusOverview.tsx
index 89e7b5b59c4..fac97d44f48 100644
--- a/airbyte-webapp/src/pages/connections/StreamStatusPage/ConnectionStatusOverview.tsx
+++ b/airbyte-webapp/src/pages/connections/StreamStatusPage/ConnectionStatusOverview.tsx
@@ -23,7 +23,6 @@ const MESSAGE_BY_STATUS: Readonly<Record<ConnectionStatusIndicatorStatus, string
   error: "connection.status.error",
   actionRequired: "connection.status.actionRequired",
   disabled: "connection.status.disabled",
-  cancelled: "connection.status.cancelled",
 };
 
 export const ConnectionStatusOverview: React.FC = () => {