Connection drops if I don't ping server

Question

I have trouble, for several months now, but I never cared asking anyone why this keeps happening. Basically if I try to reach my Server in my LAN-Network, I need to ping it several times in a row, until it "engages" (Like an old car)... The connection keeps stable while I am pinging, but if I stop, the connection will get slower and starts dropping (Timeout and such stuff).

Here what my command prompt looks like (It's not in english, but I think the command below is familiar to everyone here):

C:\Users\Username>ping 192.168.8.50 -t

Disparando 192.168.8.50 com 32 bytes de dados:
Esgotado o tempo limite do pedido.
Esgotado o tempo limite do pedido.
Resposta de 192.168.8.50: bytes=32 tempo=11ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=2ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=26ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=4ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
Resposta de 192.168.8.50: bytes=32 tempo=1ms TTL=63
[... Keeps stable connection, until I stop pinging]

I need to do this everytime I want to work with my server. I keep this window in the background pinging, but that's somewhat annoying and I can't explain myself why this is happening... I tried with several different routers (TP-Link [Stock, OpenWrt, DD-Wrt], D-Link, ...). All those present the exact same behaviour.

My LAN network looks like this:

I also tried to disable the Firewall of the router entirely and nothing changed. I can't be the only one who has this problem...

Answer 1

It's been some years since I posted this question and I just stumbled at it again while looking at my questions in my profile.

I remember this problem and I solved it some days later, but totally forgot to answer it here.

The problem was that the Subnet Mask was incorrect on one of these routers/modems. If I remember right, it was 255.255.0.0 instead of 255.255.255.0 and while pinging it would force the right Subnet-Mask or something like that.