diff --git a/agent/agent.go b/agent/agent.go
index aed6652de6..ab882a80ef 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -781,11 +781,15 @@ func (a *agent) reportConnectionsLoop(ctx context.Context, aAPI proto.DRPCAgentC
 			logger.Debug(ctx, "reporting connection")
 			_, err := aAPI.ReportConnection(ctx, payload)
 			if err != nil {
-				return xerrors.Errorf("failed to report connection: %w", err)
+				// Do not fail the loop if we fail to report a connection, just
+				// log a warning.
+				// Related to https://github.com/coder/coder/issues/20194
+				logger.Warn(ctx, "failed to report connection to server", slog.Error(err))
+				// keep going, we still need to remove it from the slice
+			} else {
+				logger.Debug(ctx, "successfully reported connection")
 			}
 
-			logger.Debug(ctx, "successfully reported connection")
-
 			// Remove the payload we sent.
 			a.reportConnectionsMu.Lock()
 			a.reportConnections[0] = nil // Release the pointer from the underlying array.
@@ -816,6 +820,13 @@ func (a *agent) reportConnection(id uuid.UUID, connectionType proto.Connection_T
 		ip = host
 	}
 
+	// If the IP is "localhost" (which it can be in some cases), set it to
+	// 127.0.0.1 instead.
+	// Related to https://github.com/coder/coder/issues/20194
+	if ip == "localhost" {
+		ip = "127.0.0.1"
+	}
+
 	a.reportConnectionsMu.Lock()
 	defer a.reportConnectionsMu.Unlock()
 
diff --git a/coderd/agentapi/connectionlog.go b/coderd/agentapi/connectionlog.go
index f26f835746..bd11f9e726 100644
--- a/coderd/agentapi/connectionlog.go
+++ b/coderd/agentapi/connectionlog.go
@@ -61,6 +61,14 @@ func (a *ConnLogAPI) ReportConnection(ctx context.Context, req *agentproto.Repor
 		return nil, xerrors.Errorf("get workspace by agent id: %w", err)
 	}
 
+	// Some older clients may incorrectly report "localhost" as the IP address.
+	// Related to https://github.com/coder/coder/issues/20194
+	logIPRaw := req.GetConnection().GetIp()
+	if logIPRaw == "localhost" {
+		logIPRaw = "127.0.0.1"
+	}
+	logIP := database.ParseIP(logIPRaw) // will return null if invalid
+
 	reason := req.GetConnection().GetReason()
 	connLogger := *a.ConnectionLogger.Load()
 	err = connLogger.Upsert(ctx, database.UpsertConnectionLogParams{
@@ -73,7 +81,7 @@ func (a *ConnLogAPI) ReportConnection(ctx context.Context, req *agentproto.Repor
 		AgentName:        workspaceAgent.Name,
 		Type:             connectionType,
 		Code:             code,
-		Ip:               database.ParseIP(req.GetConnection().GetIp()),
+		Ip:               logIP,
 		ConnectionID: uuid.NullUUID{
 			UUID:  connectionID,
 			Valid: true,
diff --git a/coderd/agentapi/connectionlog_test.go b/coderd/agentapi/connectionlog_test.go
index 4a060b8f16..81d969e5ba 100644
--- a/coderd/agentapi/connectionlog_test.go
+++ b/coderd/agentapi/connectionlog_test.go
@@ -3,13 +3,11 @@ package agentapi_test
 import (
 	"context"
 	"database/sql"
-	"net"
 	"sync/atomic"
 	"testing"
 	"time"
 
 	"github.com/google/uuid"
-	"github.com/sqlc-dev/pqtype"
 	"github.com/stretchr/testify/require"
 	"go.uber.org/mock/gomock"
 	"google.golang.org/protobuf/types/known/timestamppb"
@@ -75,6 +73,9 @@ func TestConnectionLog(t *testing.T) {
 			action: agentproto.Connection_CONNECT.Enum(),
 			typ:    agentproto.Connection_JETBRAINS.Enum(),
 			time:   dbtime.Now(),
+			// Sometimes, JetBrains clients report as localhost, see
+			// https://github.com/coder/coder/issues/20194
+			ip: "localhost",
 		},
 		{
 			name:   "Reconnecting PTY Connect",
@@ -129,6 +130,12 @@ func TestConnectionLog(t *testing.T) {
 				},
 			})
 
+			expectedIPRaw := tt.ip
+			if expectedIPRaw == "localhost" {
+				expectedIPRaw = "127.0.0.1"
+			}
+			expectedIP := database.ParseIP(expectedIPRaw)
+
 			require.True(t, connLogger.Contains(t, database.UpsertConnectionLogParams{
 				Time:             dbtime.Time(tt.time).In(time.UTC),
 				OrganizationID:   workspace.OrganizationID,
@@ -146,7 +153,7 @@ func TestConnectionLog(t *testing.T) {
 					Int32: tt.status,
 					Valid: *tt.action == agentproto.Connection_DISCONNECT,
 				},
-				Ip:   pqtype.Inet{Valid: true, IPNet: net.IPNet{IP: net.ParseIP(tt.ip), Mask: net.CIDRMask(32, 32)}},
+				Ip:   expectedIP,
 				Type: agentProtoConnectionTypeToConnectionLog(t, *tt.typ),
 				DisconnectReason: sql.NullString{
 					String: tt.reason,
diff --git a/coderd/connectionlog/connectionlog.go b/coderd/connectionlog/connectionlog.go
index 1b56ffc288..b3d9e9115f 100644
--- a/coderd/connectionlog/connectionlog.go
+++ b/coderd/connectionlog/connectionlog.go
@@ -62,10 +62,6 @@ func (m *FakeConnectionLogger) Contains(t testing.TB, expected database.UpsertCo
 			t.Logf("connection log %d: expected ID %s, got %s", idx+1, expected.ID, cl.ID)
 			continue
 		}
-		if !expected.Time.IsZero() && expected.Time != cl.Time {
-			t.Logf("connection log %d: expected Time %s, got %s", idx+1, expected.Time, cl.Time)
-			continue
-		}
 		if expected.OrganizationID != uuid.Nil && cl.OrganizationID != expected.OrganizationID {
 			t.Logf("connection log %d: expected OrganizationID %s, got %s", idx+1, expected.OrganizationID, cl.OrganizationID)
 			continue
@@ -114,6 +110,18 @@ func (m *FakeConnectionLogger) Contains(t testing.TB, expected database.UpsertCo
 			t.Logf("connection log %d: expected ConnectionID %s, got %s", idx+1, expected.ConnectionID.UUID, cl.ConnectionID.UUID)
 			continue
 		}
+		if expected.DisconnectReason.Valid && cl.DisconnectReason.String != expected.DisconnectReason.String {
+			t.Logf("connection log %d: expected DisconnectReason %s, got %s", idx+1, expected.DisconnectReason.String, cl.DisconnectReason.String)
+			continue
+		}
+		if !expected.Time.IsZero() && expected.Time != cl.Time {
+			t.Logf("connection log %d: expected Time %s, got %s", idx+1, expected.Time, cl.Time)
+			continue
+		}
+		if expected.ConnectionStatus != "" && expected.ConnectionStatus != cl.ConnectionStatus {
+			t.Logf("connection log %d: expected ConnectionStatus %s, got %s", idx+1, expected.ConnectionStatus, cl.ConnectionStatus)
+			continue
+		}
 		return true
 	}